Organometallic compound and organic light-emitting device including the same

ABSTRACT

Provided are an organometallic compound and an organic light-emitting device including the organometallic compound. The organometallic compound may be represented by Formula 1. In Formula 1, L 1  may be a ligand represented by Formula 2A or 2B, and L 2  may be a monovalent organic ligand or a divalent organic ligand.

CROSS-REFERENCE TO RELATED APPLICATION

This application claims priority to and the benefit of Korean PatentApplication No. 10-2017-0058095, filed on May 10, 2017, in the KoreanIntellectual Property Office, the entire content of which isincorporated herein by reference.

BACKGROUND 1. Field

One or more embodiments relate to an organometallic compound and anorganic light-emitting device including the same.

2. Description of the Related Art

Organic light-emitting devices are self-emission devices that producefull-color images, and also have wide viewing angles, high contrastratios, short response times, and excellent characteristics in terms ofbrightness, driving voltage, and response speed, as compared to otherdevices in the art.

An example of such organic light-emitting devices may include a firstelectrode disposed on a substrate, and a hole transport region, anemission layer, an electron transport region, and a second electrode,which are sequentially disposed on the first electrode. Holes providedfrom the first electrode may move toward the emission layer through thehole transport region, and electrons provided from the second electrodemay move toward the emission layer through the electron transportregion. Carriers, such as holes and electrons, recombine in the emissionlayer to produce excitons. These excitons transition (or relax) from anexcited state to a ground state, thereby generating light.

SUMMARY

Aspects of embodiments of the present disclosure provide a novelorganometallic compound and an organic light-emitting device includingthe same.

Additional aspects of embodiments will be set forth in part in thedescription which follows and, in part, will be apparent from thedescription, or may be learned by practice of the presented embodiments.

An aspect of an embodiment of the present disclosure provides anorganometallic compound represented by Formula 1 below:

M in Formula 1 may be Pt, Pd, Ir, or Os,

in Formula 1, L₁ may be a ligand represented by Formula 2A or 2B, and n1may be 1 or 2, wherein, when n1 is two, two L₁(s) may be identical to ordifferent from each other,

in Formula 1, L₂ may be a monovalent organic ligand or a divalentorganic ligand, and n2 may be 1 or 2,

the sum of n1 and n2 in Formula 1 may be 1, 2, or 3,

^(*1), ^(*2), and ^(*3) in Formula 2A and ^(*1), ^(*2), ^(*3), and ^(*4)in Formula 2B each indicate a binding site to M in Formula 1,

X₁ may be N or C, X₂ may be N or C, X₃ may be N or C, and X₄ may be N orC,

Y₁ to Y₈ may each independently be N or C,

a bond between X₁ and Y₁ may be a single bond or a double bond,

a bond between X₁ and Y₂ may be a single bond or a double bond,

a bond between X₂ and Y₃ may be a single bond or a double bond,

a bond between X₂ and Y₄ may be a single bond or a double bond,

a bond between X₃ and Y₅ may be a single bond or a double bond,

a bond between X₃ and Y₆ may be a single bond or a double bond,

rings A₁ to A₄ may each independently be a C₅-C₃₀ carbocyclic group or aC₂-C₆₀ heterocyclic group,

T₁ to T₃ may each independently be selected from *—N[(L)_(a5)-(R₁₅)]—*′,*—B(R₁₅)—*′, *—P(R₁₅)—*′, *—C(R₁₅)(R₁₅)—*′, *—Si(R₁₅)(R₁₅)—*′,*—Ge(R₁₅)(R₁₆)—*′, *—S—*′, *—Se—*′, * O—*′, *—C(═O)—*′, *—S(═O)—*′,*—S(═O)₂—*′, *—C(R₁₅)=*′, *═C(R₁₅)—*′, *—C(R₁₅)═C(R₁₆)—*′, C(═S)—*′, and*—C≡C—*′,

a5 may be selected from 1 to 3, wherein, when a5 is two or more, two ormore L₅(s) may be identical to or different from each other,

R₁₅ and R₁₆ may optionally be linked to a neighboring substituentselected from R₁₁ to R₁₄ to form a substituted or unsubstituted C₅-C₃₀carbocyclic group or a substituted or unsubstituted C₁-C₃₀ heterocyclicgroup,

b1 to b4 may each independently be 0, 1, 2, or 3, wherein, when b1 iszero, *-(T₁)_(b1)-*′ may be a single bond, when b2 is zero,*-(T₂)_(b2)-*′ may be a single bond, when b3 is zero, *-(T₃)_(b3)-*′ maybe a single bond, and when b4 is 0, *-(T₄)_(b4)-*′ may be a single bond,

*and *′ each indicate a binding site to a neighboring atom,

Z₁ to Z₄ may each be represented by Formula 3,

c1 to c4 may each independently be 0, 1, 2, or 3,

the sum of c1, c2, and c3 in Formula 2A may be one or more,

the sum of c1, c2, c3, and c4 in Formula 2B may be one or more,

T₅ in Formula 3 may be a substituted or unsubstituted C₅-C₃₀ carbocyclicgroup or a substituted or unsubstituted C₂-C₆₀ heterocyclic group,

b5 may be an integer from 0 to 5,

X₅ may be O, S, or N(R₃),

R₁ to R₃ and R₁₁ to R₁₆ may each independently be selected fromhydrogen, deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group,a nitro group, an amidino group, a hydrazino group, a hydrazono group, asubstituted or unsubstituted C₁-C₆₀ alkyl group, a substituted orunsubstituted C₂-C₆₀ alkenyl group, a substituted or unsubstitutedC₂-C₆₀ alkynyl group, a substituted or unsubstituted C₁-C₆₀ alkoxygroup, a substituted or unsubstituted C₃-C₁₀ cycloalkyl group, asubstituted or unsubstituted C₁-C₁₀ heterocycloalkyl group, asubstituted or unsubstituted C₃-C₁₀ cycloalkenyl group, a substituted orunsubstituted C₁-C₁₀ heterocycloalkenyl group, a substituted orunsubstituted C₆-C₆₀ aryl group, a substituted or unsubstituted C₆-C₆₀aryloxy group, a substituted or unsubstituted C₆-C₆₀ arylthio group, asubstituted or unsubstituted C₁-C₆₀ heteroaryl group, a substituted orunsubstituted monovalent non-aromatic condensed polycyclic group, asubstituted or unsubstituted monovalent non-aromatic condensedheteropolycyclic group, —Si(Q₁)(Q₂)(Q₃), —N(Q₁)(Q₂), —B(Q₁)(Q₂),—C(═O)(Q₁), —S(═O)₂(Q₁), and —P(═O)(Q₁)(Q₂),

at least one substituent of the substituted C₁-C₆₀ alkyl group, thesubstituted C₂-C₆₀ alkenyl group, the substituted C₂-C₆₀ alkynyl group,the substituted C₁-C₆₀ alkoxy group, the substituted C₃-C₁₀ cycloalkylgroup, the substituted C₁-C₁₀ heterocycloalkyl group, the substitutedC₃-C₁₀ cycloalkenyl group, the substituted C₁-C₁₀ heterocycloalkenylgroup, the substituted C₆-C₆₀ aryl group, the substituted C₆-C₆₀ aryloxygroup, the substituted C₆-C₆₀ arylthio group, the substituted C₁-C₆₀heteroaryl group, the substituted monovalent non-aromatic condensedpolycyclic group, the substituted monovalent non-aromatic condensedheteropolycyclic group, the substituted C₄-C₆₀ carbocyclic group, andthe substituted C₂-C₆₀ heterocyclic group may be selected from:

deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, a nitrogroup, an amidino group, a hydrazino group, a hydrazono group, a C₁-C₆₀alkyl group, a C₂-C₆₀ alkenyl group, a C₂-C₆₀ alkynyl group, and aC₁-C₆₀ alkoxy group;

a C₁-C₆₀ alkyl group, a C₂-C₆₀ alkenyl group, a C₂-C₆₀ alkynyl group,and a C₁-C₆₀ alkoxy group, each substituted with at least one selectedfrom deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, anitro group, an amidino group, a hydrazino group, a hydrazono group, aC₃-C₁₀ cycloalkyl group, a C₁-C₁₀ heterocycloalkyl group, a C₃-C₁₀cycloalkenyl group, a C₁-C₁₀ heterocycloalkenyl group, a C₆-C₆₀ arylgroup, a C₆-C₆₀ aryloxy group, a C₆-C₆₀ arylthio group, a C₁-C₆₀heteroaryl group, a monovalent non-aromatic condensed polycyclic group,a monovalent non-aromatic condensed heteropolycyclic group,—Si(Q₁₁)(Q₁₂)(Q₁₃), —N(Q₁₁)(Q₁₂), —B(Q₁₁)(Q₁₂), —C(═O)(Q₁₁),—S(═O)₂(Q₁₁), and —P(═O)(Q₁₁)(Q₁₂);

a C₃-C₁₀ cycloalkyl group, a C₁-C₁₀ heterocycloalkyl group, a C₃-C₁₀cycloalkenyl group, a C₁-C₁₀ heterocycloalkenyl group, a C₆-C₆₀ arylgroup, a C₆-C₆₀ aryloxy group, a C₆-C₆₀ arylthio group, a C₁-C₆₀heteroaryl group, a monovalent non-aromatic condensed polycyclic group,and a monovalent non-aromatic condensed heteropolycyclic group;

a C₃-C₁₀ cycloalkyl group, a C₁-C₁₀ heterocycloalkyl group, a C₃-C₁₀cycloalkenyl group, a C₁-C₁₀ heterocycloalkenyl group, a C₆-C₆₀ arylgroup, a C₆-C₆₀ aryloxy group, a C₆-C₆₀ arylthio group, a C₁-C₆₀heteroaryl group, a monovalent non-aromatic condensed polycyclic group,and a monovalent non-aromatic condensed heteropolycyclic group, eachsubstituted with at least one selected from deuterium, —F, —Cl, —Br, —I,a hydroxyl group, a cyano group, a nitro group, an amidino group, ahydrazino group, a hydrazono group, a C₁-C₆₀ alkyl group, a C₂-C₆₀alkenyl group, a C₂-C₆₀ alkynyl group, a C₁-C₆₀ alkoxy group, a C₃-C₁₀cycloalkyl group, a C₁-C₁₀ heterocycloalkyl group, a C₃-C₁₀ cycloalkenylgroup, a C₁-C₁₀ heterocycloalkenyl group, a C₆-C₆₀ aryl group, a C₆-C₆₀aryloxy group, a C₆-C₆₀ arylthio group, a C₁-C₆₀ heteroaryl group, amonovalent non-aromatic condensed polycyclic group, a monovalentnon-aromatic condensed heteropolycyclic group, —Si(Q₂₁)(Q₂₂)(Q₂₃),—N(Q₂₁)(Q₂₂), —B(Q₂₁)(Q₂₂), —C(═O)(Q₂₁), —S(═O)₂(Q₂₁), and—P(═O)(Q₂₁)(Q₂₂); and

—Si(Q₃₁)(Q₃₂)(Q₃₃), —N(Q₃₁)(Q₃₂), —B(Q₃₁)(Q₃₂), —C(═O)(Q₃₁),—S(═O)₂(Q₃₁), and —P(═O)(Q₃₁)(Q₃₂), and

Q₁ to Q₃, Q₁₁ to Q₁₃, Q₂₁ to Q₂₃, and Q₃₁ to Q₃₃ may each independentlybe selected from hydrogen, deuterium, —F, —Cl, —Br, —I, a hydroxylgroup, a cyano group, a nitro group, an amidino group, a hydrazinogroup, a hydrazono group, a C₁-C₆₀ alkyl group, a C₂-C₆₀ alkenyl group,a C₂-C₆₀ alkynyl group, a C₁-C₆₀ alkoxy group, a C₃-C₁₀ cycloalkylgroup, a C₁-C₁₀ heterocycloalkyl group, a C₃-C₁₀ cycloalkenyl group, aC₁-C₁₀ heterocycloalkenyl group, a C₆-C₆₀ aryl group, a C₁-C₆₀heteroaryl group, a monovalent non-aromatic condensed polycyclic group,a monovalent non-aromatic condensed heteropolycyclic group, a biphenylgroup, and a terphenyl group.

Another aspect of an embodiment of the present disclosure provides anorganic light-emitting device including: a first electrode; a secondelectrode; and an organic layer between the first electrode and thesecond electrode and including an emission layer, wherein the organiclayer includes at least one of the organometallic compound.

BRIEF DESCRIPTION OF THE DRAWING

These and/or other aspects will become apparent and more readilyappreciated from the following description of the embodiments, taken inconjunction with the accompanying drawing which is a schematic view ofan organic light-emitting device according to an embodiment.

DETAILED DESCRIPTION

Reference will now be made in detail to embodiments, examples of whichare illustrated in the accompanying drawing, wherein like referencenumerals refer to like elements throughout. In this regard, the presentembodiments may have different forms and should not be construed asbeing limited to the descriptions set forth herein. Accordingly, theembodiments are merely described below, by referring to the figures, toexplain aspects of embodiments of the present description. As usedherein, the term “and/or” includes any and all combinations of one ormore of the associated listed items. Expressions such as “at least oneof,” when preceding a list of elements, modify the entire list ofelements and do not modify the individual elements of the list.

An organometallic compound according to an embodiment is represented byFormula 1 below:

M(L₁)_(n1)(L₂)_(n2).  Formula 1

M in Formula 1 may be platinum (Pt), palladium (Pd), iridium (Ir), orosmium (Os).

In one embodiment, M may be platinum, but embodiments of the presentdisclosure are not limited thereto.

In Formula 1, L₁ may be a ligand represented by Formula 2A or 2B, and n1may be 1 or 2, wherein, when n1 is two, two L₁(s) may be identical to ordifferent from each other.

In one embodiment, n1 is 1, but embodiments of the present disclosureare not limited thereto.

In Formula 1, L₂ may be a monovalent organic ligand or a divalentorganic ligand, and n2 may be 0, 1, or 2.

In one embodiment, L₂ may be a monovalent organic ligand, butembodiments of the present disclosure are not limited thereto.

In one or more embodiments, L₂ may be selected from ligands representedby Formulae 3A to 3F, but embodiments of the present disclosure are notlimited thereto:

In Formulae 3A to 3F,

X₁₁ may be N or C(R₃₁), and X₁₂ may be N or C(R₃₂),

L₁₁ to L₂₁ may each independently be selected from a substituted orunsubstituted C₃-C₁₀ cycloalkylene group, a substituted or unsubstitutedC₁-C₁₀ heterocycloalkylene group, a substituted or unsubstituted C₃-C₁₀cycloalkenylene group, a substituted or unsubstituted C₁-C₁₀heterocycloalkenylene group, a substituted or unsubstituted C₆-C₆₀arylene group, a substituted or unsubstituted C₁-C₆₀ heteroarylenegroup, a substituted or unsubstituted divalent non-aromatic condensedpolycyclic group, and a substituted or unsubstituted divalentnon-aromatic condensed heteropolycyclic group,

a11 to a21 may each independently be an integer from 0 to 3,

Ar₁₁ and Ar₁₂ may each independently be selected from a substituted orunsubstituted C₃-C₁₀ cycloalkyl group, a substituted or unsubstitutedC₁-C₁₀ heterocycloalkyl group, a substituted or unsubstituted C₃-C₁₀cycloalkenyl group, a substituted or unsubstituted C₁-C₁₀heterocycloalkenyl group, a substituted or unsubstituted C₆-C₆₀ arylgroup, a substituted or unsubstituted C₁-C₆₀ heteroaryl group, asubstituted or unsubstituted monovalent non-aromatic condensedpolycyclic group, and a substituted or unsubstituted monovalentnon-aromatic condensed heteropolycyclic group,

R₃₁ to R₃₂ may each independently be selected from hydrogen, deuterium,—F, —Cl, —Br, —I, a hydroxyl group, a cyano group, a nitro group, anamidino group, a hydrazino group, a hydrazono group, a substituted orunsubstituted C₁-C₆₀ alkyl group, a substituted or unsubstituted C₂-C₆₀alkenyl group, a substituted or unsubstituted C₂-C₆₀ alkynyl group, asubstituted or unsubstituted C₁-C₆₀ alkoxy group, a substituted orunsubstituted C₃-C₁₀ cycloalkyl group, a substituted or unsubstitutedC₁-C₁₀ heterocycloalkyl group, a substituted or unsubstituted C₃-C₁₀cycloalkenyl group, a substituted or unsubstituted C₁-C₁₀heterocycloalkenyl group, a substituted or unsubstituted C₆-C₆₀ arylgroup, a substituted or unsubstituted C₆-C₆₀ aryloxy group, asubstituted or unsubstituted C₆-C₆₀ arylthio group, a substituted orunsubstituted C₁-C₆₀ heteroaryl group, a substituted or unsubstitutedmonovalent non-aromatic condensed polycyclic group, a substituted orunsubstituted monovalent non-aromatic condensed heteropolycyclic group,—Si(Q₁₁)(Q₁₂)(Q₁₃), —N(Q₁₁)(Q₁₂), —B(Q₁₁)(Q₁₂), —C(═O)(Q₁₁),—S(═O)₂(Q₁₁), and —P(═O)(Q₁₁)(Q₁₂),

R₃₁ and R₃₂ may optionally be linked to form a saturated or unsaturatedring, and R₃₃ and R₃₄ may optionally be linked to form a saturated orunsaturated ring,

X₂₁ may be selected from —F, —Cl, —Br, and —I,

*″ indicates a binding site to M in Formula 1,

at least one substituent of the substituted C₃-C₁₀ cycloalkylene group,the substituted C₁-C₁₀ heterocycloalkylene group, the substituted C₃-C₁₀cycloalkenylene group, the substituted C₁-C₁₀ heterocycloalkenylenegroup, the substituted C₆-C₆₀ arylene group, the substituted C₁-C₆₀heteroarylene group, the substituted divalent non-aromatic condensedpolycyclic group, the substituted divalent non-aromatic condensedheteropolycyclic group, the substituted C₁-C₆₀ alkyl group, thesubstituted C₂-C₆₀ alkenyl group, the substituted C₂-C₆₀ alkynyl group,the substituted C₁-C₆₀ alkoxy group, the substituted C₃-C₁₀ cycloalkylgroup, the substituted C₁-C₁₀ heterocycloalkyl group, the substitutedC₃-C₁₀ cycloalkenyl group, the substituted C₁-C₁₀ heterocycloalkenylgroup, the substituted C₆-C₆₀ aryl group, the substituted C₆-C₆₀ aryloxygroup, the substituted C₆-C₆₀ arylthio group, the substituted C₁-C₆₀heteroaryl group, the substituted monovalent non-aromatic condensedpolycyclic group, and the substituted monovalent non-aromatic condensedheteropolycyclic group may be selected from:

deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, a nitrogroup, an amidino group, a hydrazino group, a hydrazono group, a C₁-C₆₀alkyl group, a C₂-C₆₀ alkenyl group, a C₂-C₆₀ alkynyl group, and aC₁-C₆₀ alkoxy group;

a C₁-C₆₀ alkyl group, a C₂-C₆₀ alkenyl group, a C₂-C₆₀ alkynyl group,and a C₁-C₆₀ alkoxy group, each substituted with at least one selectedfrom deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, anitro group, an amidino group, a hydrazino group, a hydrazono group, aC₃-C₁₀ cycloalkyl group, a C₁-C₁₀ heterocycloalkyl group, a C₃-C₁₀cycloalkenyl group, a C₁-C₁₀ heterocycloalkenyl group, a C₆-C₆₀ arylgroup, a C₆-C₆₀ aryloxy group, a C₆-C₆₀ arylthio group, a C₁-C₆₀heteroaryl group, a monovalent non-aromatic condensed polycyclic group,a monovalent non-aromatic condensed heteropolycyclic group,—Si(Q₁₁)(Q₁₂)(Q₁₃), —N(Q₁₁)(Q₁₂), —B(Q₁₁)(Q₁₂), —C(═O)(Q₁₁),—S(═O)₂(Q₁₁), and —P(═O)(Q₁₁)(Q₁₂);

a C₃-C₁₀ cycloalkyl group, a C₁-C₁₀ heterocycloalkyl group, a C₃-C₁₀cycloalkenyl group, a C₁-C₁₀ heterocycloalkenyl group, a C₆-C₆₀ arylgroup, a C₆-C₆₀ aryloxy group, a C₆-C₆₀ arylthio group, a C₁-C₆₀heteroaryl group, a monovalent non-aromatic condensed polycyclic group,and a monovalent non-aromatic condensed heteropolycyclic group;

a C₃-C₁₀ cycloalkyl group, a C₁-C₁₀ heterocycloalkyl group, a C₃-C₁₀cycloalkenyl group, a C₁-C₁₀ heterocycloalkenyl group, a C₆-C₆₀ arylgroup, a C₆-C₆₀ aryloxy group, a C₆-C₆₀ arylthio group, a C₁-C₆₀heteroaryl group, a monovalent non-aromatic condensed polycyclic group,and a monovalent non-aromatic condensed heteropolycyclic group, eachsubstituted with at least one selected from deuterium, —F, —Cl, —Br, —I,a hydroxyl group, a cyano group, a nitro group, an amidino group, ahydrazino group, a hydrazono group, a C₁-C₆₀ alkyl group, a C₂-C₆₀alkenyl group, a C₂-C₆₀ alkynyl group, a C₁-C₆₀ alkoxy group, a C₃-C₁₀cycloalkyl group, a C₁-C₁₀ heterocycloalkyl group, a C₃-C₁₀ cycloalkenylgroup, a C₁-C₁₀ heterocycloalkenyl group, a C₆-C₆₀ aryl group, a C₆-C₆₀aryloxy group, a C₆-C₆₀ arylthio group, a C₁-C₆₀ heteroaryl group, amonovalent non-aromatic condensed polycyclic group, a monovalentnon-aromatic condensed heteropolycyclic group, —Si(Q₂₁)(Q₂₂)(Q₂₃),—N(Q₂₁)(Q₂₂), —B(Q₂₁)(Q₂₂), —C(═O)(Q₂₁), —S(═O)₂(Q₂₁), and—P(═O)(Q₂₁)(Q₂₂); and

—Si(Q₃₁)(Q₃₂)(Q₃₃), —N(Q₃₁)(Q₃₂), —B(Q₃₁)(Q₃₂), —C(═O)(Q₃₁),—S(═O)₂(Q₃₁), and —P(═O)(Q₃₁)(Q₃₂), and

Q₁ to Q₃, Q₁₁ to Q₁₃, Q₂₁ to Q₂₃, and Q₃₁ to Q₃₃ may each independentlybe selected from hydrogen, deuterium, —F, —Cl, —Br, —I, a hydroxylgroup, a cyano group, a nitro group, an amidino group, a hydrazinogroup, a hydrazono group, a C₁-C₆₀ alkyl group, a C₂-C₆₀ alkenyl group,a C₂-C₆₀ alkynyl group, a C₁-C₆₀ alkoxy group, a C₃-C₁₀ cycloalkylgroup, a C₁-C₁₀ heterocycloalkyl group, a C₃-C₁₀ cycloalkenyl group, aC₁-C₁₀ heterocycloalkenyl group, a C₆-C₆₀ aryl group, a C₁-C₆₀heteroaryl group, a monovalent non-aromatic condensed polycyclic group,a monovalent non-aromatic condensed heteropolycyclic group, a biphenylgroup, and a terphenyl group.

In one embodiment, L₂ may be selected from —F, —Cl, —Br, and a cyanogroup.

In one embodiment, n2 is 0, but embodiments of the present disclosureare not limited thereto.

The sum of n1 and n2 in Formula 1 may be 1, 2, or 3.

In one embodiment, the sum of n1 and n2 may be 1 or 2, but embodimentsof the present disclosure are not limited thereto.

^(*1), ^(*2), and ^(*3) in Formula 2A and ^(*1), ^(*2), ^(*3), and ^(*4)in Formula 2B each indicate a binding site to M in Formula 1.

In Formulae 2A and 2B, X₁ may be N or C, X₂ may be N or C, X₃ may be Nor C, and X₄ may be N or C.

Y₁ to Y₈ in Formulae 2A and 2B may each independently be N or C.

In Formulae 2A and 2B,

a bond between X₁ and Y₁ may be a single bond or a double bond,

a bond between X₁ and Y₂ may be a single bond or a double bond,

a bond between X₂ and Y₃ may be a single bond or a double bond,

a bond between X₂ and Y₄ may be a single bond or a double bond,

a bond between X₃ and Y₅ may be a single bond or a double bond, and

a bond between X₃ and Y₆ may be a single bond or a double bond.

Rings A₁ to A₄ in Formulae 2A and 2B may each independently be a C₅-C₃₀carbocyclic group or a C₂-C₆₀ heterocyclic group.

In one embodiment, rings A₁ to A₄ may each independently be selectedfrom a benzene group, a naphthalene group, an anthracene group, aphenanthrene group, a fluorene group, a phenalene group, a pyrene group,a fluoranthene group, a tetracene group, a chrysene group, atriphenylene group, a benzofluorene group, a perylene group, an indenegroup, an acenaphthene group, a biphenyl group, a terphenyl group, apyridine group, a pyrimidine group, a pyrazine group, a pyridazinegroup, a triazine group, a quinoline group, an isoquinoline group, aquinoxaline group, a quinazoline group, a phenanthroline group, apyrazole group, an imidazole group, a triazole group, an oxazole group,an isoxazole group, a thiazole group, an isothiazole group, anoxadiazole group, a thiadiazol group, a benzopyrazole group, abenzimidazole group, an imidazopyrazinyl group, a benzoxazole group, abenzothiazole group, a benzoxadiazole group, and a benzothiadiazolgroup.

In one or more embodiments, rings A₁ to A₄ may each independently beselected from a benzene group, a pyridine group, a pyrimidine group, atriazine group, a pyrazole group, an imidazole group, a triazole group,an oxazole group, an isoxazole group, a thiazole group, an isothiazolegroup, an oxadiazole group, a thiadiazol group, a benzopyrazole group, abenzimidazole group, an imidazopyrazinyl group, a benzoxazole group, abenzothiazole group, a benzoxadiazole group, and a benzothiadiazolgroup.

In one or more embodiments, rings A₁ to A₄ may each independently beselected from a benzene group, a pyridine group, a pyrimidine group, atriazine group, a pyrazole group, an imidazole group, a triazole group,a benzopyrazole group, a benzimidazole group, and an imidazopyrazinylgroup, but embodiments of the present disclosure are not limitedthereto.

T₁ to T₃ in Formulae 2A and 2B may each independently be selected from*—N[(L)_(a5)-(R₁₅)]—*′, *—B(R₁₅)—*′, *—P(R₁₅)—*′, *—C(R₁₅)(R₁₅)—*′,*—Si(R₁₅)(R₁₅)—*′, *—Ge(R₁₅)(R₁₆)—*′, *—S—*′, *—Se—*′, *—O—*′,*—C(═O)—*′, *—S(═O)—*′, *—S(═O)₂—*′, *—C(R₁₅)=*′, *═C(R₁₅)—*′,*—C(R₁₅)═C(R₁₆)—*′, *—C(═S)—*′, and *—C≡C—*′,

a5 may be selected from 1 to 3, wherein, when a5 is two or more, two ormore L₅(s) may be identical to or different from each other, and

R₁₅ and R₁₆ may optionally be linked to a neighboring substituentselected from R₁₁ to R₁₄ to form a substituted or unsubstituted C₅-C₃₀carbocyclic group or a substituted or unsubstituted C₁-C₃₀ heterocyclicgroup.

In one embodiment, when at least one of T₁ to T₃ is*—N[(L₅)_(a5)-(R₁₅)]—*′, R₁₅ may be a substituted or unsubstitutedC₁-C₆₀ aryl group, or may optionally be linked to a neighboringsubstituent selected from R₁₁ to R₁₄ to form a substituted orunsubstituted C₁-C₆₀ heterocyclic group.

In one or more embodiments, R₁₅ may be a substituted or unsubstitutedphenyl group, or may optionally be linked to one of L₁ to L₄ to form asubstituted or unsubstituted carbazole ring or a substituted orunsubstituted azacarbazole ring, but embodiments of the presentdisclosure are not limited thereto.

b1 to b4 in Formulae 2A and 2B may each independently be 0, 1, 2, or 3.When b1 is zero, *-(T₁)_(b1)-*′ may be a single bond, when b2 is zero,*-(T₂)_(b2)-*′ may be a single bond, when b3 is zero, *-(T₃)_(b3)-*′ maybe a single bond, when b4 is zero, *-(T₄)_(b4)-*′ may be a single bond,and * and *′ each indicate a binding site to a neighboring atom.

In Formulae 2A and 2B, Z₁ to Z₄ may each be represented by Formula 3,and c1 to c4 may each independently be 0, 1, 2, or 3.

In Formulae 2A and 2B, the sum of c1, c2, and c3 in Formula 2A may beone or more, and the sum of c1, c2, c3, and c4 in Formula 2B may be oneor more.

T₅ in Formula 3 may be a substituted or unsubstituted C₅-C₃₀ carbocyclicgroup or a substituted or unsubstituted C₂-C₆₀ heterocyclic group.

In one embodiment, rings A₁ to A₄ may each independently be selectedfrom:

a benzene group, a naphthalene group, an anthracene group, aphenanthrene group, a fluorene group, a phenalene group, a pyrene group,a fluoranthene group, a tetracene group, a chrysene group, atriphenylene group, a benzofluorene group, a perylene group, an indenegroup, an acenaphthene group, a biphenyl group, a terphenyl group, apyridine group, a pyrimidine group, a pyrazine group, a pyridazinegroup, a triazine group, a quinoline group, an isoquinoline group, aquinoxaline group, a quinazoline group, a phenanthroline group, apyrazole group, an imidazole group, a triazole group, an oxazole group,an isoxazole group, a thiazole group, an isothiazole group, anoxadiazole group, a thiadiazol group, a benzopyrazole group, abenzimidazole group, an imidazopyrazinyl group, a benzoxazole group, abenzothiazole group, a benzoxadiazole group, and a benzothiadiazolgroup; and

a benzene group, a naphthalene group, an anthracene group, aphenanthrene group, a fluorene group, a phenalene group, a pyrene group,a fluoranthene group, a tetracene group, a chrysene group, atriphenylene group, a benzofluorene group, a perylene group, an indenegroup, an acenaphthene group, a biphenyl group, a terphenyl group, apyridine group, a pyrimidine group, a pyrazine group, a pyridazinegroup, a triazine group, a quinoline group, an isoquinoline group, aquinoxaline group, a quinazoline group, a phenanthroline group, apyrazole group, an imidazole group, a triazole group, an oxazole group,an isoxazole group, a thiazole group, an isothiazole group, anoxadiazole group, a thiadiazol group, a benzopyrazole group, abenzimidazole group, an imidazopyrazinyl group, a benzoxazole group, abenzothiazole group, a benzoxadiazole group, and a benzothiadiazolgroup, each substituted with at least one substituent selected fromdeuterium, —CD₃, —CD₂H, —CDH₂, —F, —Cl, —Br, a cyano group, —CF₃, —CF₂H,—CFH₂, a hydroxyl group, a cyano group, a nitro group, an amidino group,a hydrazino group, a hydrazono group, a C₁-C₂₀ alkyl group, a C₂-C₂₀alkenyl group, a C₂-C₂₀ alkynyl group, a C₁-C₂₀ alkoxy group, acyclopentyl group, a cyclohexyl group, a cycloheptyl group, a cyclooctylgroup, an adamantanyl group, a norbornanyl group, a norbornenyl group, acyclopentenyl group, a cyclohexenyl group, a cycloheptenyl group, aphenyl group, a naphthyl group, an anthracenyl group, a phenanthrenylgroup, a fluorenyl group, a phenalenyl group, a pyrenyl group, afluoranthenyl group, a tetracenyl group, a chrysenyl group, atriperylenyl group, a benzofluorenyl group, a perylenyl group, anindenyl group, an acenaphthylene group, a biphenyl group, a terphenylgroup, a pyridyl group, a pyrimidyl group, a pyrazinyl group, apyridazinyl group, a triazinyl group, a quinolinyl group, anisoquinolinyl group, a quinoxalinyl group, a quinazolinyl group, aphenanthrolinyl group, a pyrazolyl group, an imidazolyl group, atriazolyl group, an oxazolyl group, an isoxazolyl group, a thiazolylgroup, an isothiazolyl group, an oxadiazolyl group, a thiadiazolylgroup, a benzopyrazolyl group, a benzimidazolyl group, animidazopyrazinyl group, a benzoxazolyl group, a benzothiazole group, abenzoxadiazole group, and a benzothiadiazolyl group,

but embodiments of the present disclosure are not limited thereto.

b5 in Formula 3 may be an integer from 0 to 5.

In one embodiment, b5 may be 0, 1, or 2.

In one or more embodiments, b5 may be 0.

X₅ in Formula 3 may be O, S, or N(R₃).

R₁ to R₃ and R₁₁ to R₁₆ in Formula 3 may each independently be selectedfrom hydrogen, deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyanogroup, a nitro group, an amidino group, a hydrazino group, a hydrazonogroup, a substituted or unsubstituted C₁-C₆₀ alkyl group, a substitutedor unsubstituted C₂-C₆₀ alkenyl group, a substituted or unsubstitutedC₂-C₆₀ alkynyl group, a substituted or unsubstituted C₁-C₆₀ alkoxygroup, a substituted or unsubstituted C₃-C₁₀ cycloalkyl group, asubstituted or unsubstituted C₁-C₁₀ heterocycloalkyl group, asubstituted or unsubstituted C₃-C₁₀ cycloalkenyl group, a substituted orunsubstituted C₁-C₁₀ heterocycloalkenyl group, a substituted orunsubstituted C₆-C₆₀ aryl group, a substituted or unsubstituted C₆-C₆₀aryloxy group, a substituted or unsubstituted C₆-C₆₀ arylthio group, asubstituted or unsubstituted C₁-C₆₀ heteroaryl group, a substituted orunsubstituted monovalent non-aromatic condensed polycyclic group, asubstituted or unsubstituted monovalent non-aromatic condensedheteropolycyclic group, —Si(Q₁)(Q₂)(Q₃), —N(Q₁)(Q₂), —B(Q₁)(Q₂),—C(═O)(Q₁), —S(═O)₂(Q₁), and —P(═O)(Q₁)(Q₂),

at least one substituent of the substituted C₁-C₆₀ alkyl group, thesubstituted C₂-C₆₀ alkenyl group, the substituted C₂-C₆₀ alkynyl group,the substituted C₁-C₆₀ alkoxy group, the substituted C₃-C₁₀ cycloalkylgroup, the substituted C₁-C₁₀ heterocycloalkyl group, the substitutedC₃-C₁₀ cycloalkenyl group, the substituted C₁-C₁₀ heterocycloalkenylgroup, the substituted C₆-C₆₀ aryl group, the substituted C₆-C₆₀ aryloxygroup, the substituted C₆-C₆₀ arylthio group, the substituted C₁-C₆₀heteroaryl group, the substituted monovalent non-aromatic condensedpolycyclic group, the substituted monovalent non-aromatic condensedheteropolycyclic group, the substituted C₄-C₆₀ carbocyclic group, andthe substituted C₂-C₆₀ heterocyclic group may be selected from:

deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, a nitrogroup, an amidino group, a hydrazino group, a hydrazono group, a C₁-C₆₀alkyl group, a C₂-C₆₀ alkenyl group, a C₂-C₆₀ alkynyl group, and aC₁-C₆₀ alkoxy group;

a C₁-C₆₀ alkyl group, a C₂-C₆₀ alkenyl group, a C₂-C₆₀ alkynyl group,and a C₁-C₆₀ alkoxy group, each substituted with at least one selectedfrom deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, anitro group, an amidino group, a hydrazino group, a hydrazono group, aC₃-C₁₀ cycloalkyl group, a C₁-C₁₀ heterocycloalkyl group, a C₃-C₁₀cycloalkenyl group, a C₁-C₁₀ heterocycloalkenyl group, a C₆-C₆₀ arylgroup, a C₆-C₆₀ aryloxy group, a C₆-C₆₀ arylthio group, a C₁-C₆₀heteroaryl group, a monovalent non-aromatic condensed polycyclic group,a monovalent non-aromatic condensed heteropolycyclic group,—Si(Q₁₁)(Q₁₂)(Q₁₃), —N(Q₁₁)(Q₁₂), —B(Q₁₁)(Q₁₂), —C(═O)(Q₁₁),—S(═O)₂(Q₁₁), and —P(═O)(Q₁₁)(Q₁₂);

a C₃-C₁₀ cycloalkyl group, a C₁-C₁₀ heterocycloalkyl group, a C₃-C₁₀cycloalkenyl group, a C₁-C₁₀ heterocycloalkenyl group, a C₆-C₆₀ arylgroup, a C₆-C₆₀ aryloxy group, a C₆-C₆₀ arylthio group, a C₁-C₆₀heteroaryl group, a monovalent non-aromatic condensed polycyclic group,and a monovalent non-aromatic condensed heteropolycyclic group;

a C₃-C₁₀ cycloalkyl group, a C₁-C₁₀ heterocycloalkyl group, a C₃-C₁₀cycloalkenyl group, a C₁-C₁₀ heterocycloalkenyl group, a C₆-C₆₀ arylgroup, a C₆-C₆₀ aryloxy group, a C₆-C₆₀ arylthio group, a C₁-C₆₀heteroaryl group, a monovalent non-aromatic condensed polycyclic group,and a monovalent non-aromatic condensed heteropolycyclic group, eachsubstituted with at least one selected from deuterium, —F, —Cl, —Br, —I,a hydroxyl group, a cyano group, a nitro group, an amidino group, ahydrazino group, a hydrazono group, a C₁-C₆₀ alkyl group, a C₂-C₆₀alkenyl group, a C₂-C₆₀ alkynyl group, a C₁-C₆₀ alkoxy group, a C₃-C₁₀cycloalkyl group, a C₁-C₁₀ heterocycloalkyl group, a C₃-C₁₀ cycloalkenylgroup, a C₁-C₁₀ heterocycloalkenyl group, a C₆-C₆₀ aryl group, a C₆-C₆₀aryloxy group, a C₆-C₆₀ arylthio group, a C₁-C₆₀ heteroaryl group, amonovalent non-aromatic condensed polycyclic group, a monovalentnon-aromatic condensed heteropolycyclic group, —Si(Q₂₁)(Q₂₂)(Q₂₃),—N(Q₂₁)(Q₂₂), —B(Q₂₁)(Q₂₂), —C(═O)(Q₂₁), —S(═O)₂(Q₂₁), and—P(═O)(Q₂₁)(Q₂₂); and

—Si(Q₃₁)(Q₃₂)(Q₃₃), —N(Q₃₁)(Q₃₂), —B(Q₃₁)(Q₃₂), —C(═O)(Q₃₁),—S(═O)₂(Q₃₁), and —P(═O)(Q₃₁)(Q₃₂), and

Q₁ to Q₃, Q₁₁ to Q₁₃, Q₂₁ to Q₂₃, and Q₃₁ to Q₃₃ may each independentlybe selected from hydrogen, deuterium, —F, —Cl, —Br, —I, a hydroxylgroup, a cyano group, a nitro group, an amidino group, a hydrazinogroup, a hydrazono group, a C₁-C₆₀ alkyl group, a C₂-C₆₀ alkenyl group,a C₂-C₆₀ alkynyl group, a C₁-C₆₀ alkoxy group, a C₃-C₁₀ cycloalkylgroup, a C₁-C₁₀ heterocycloalkyl group, a C₃-C₁₀ cycloalkenyl group, aC₁-C₁₀ heterocycloalkenyl group, a C₆-C₆₀ aryl group, a C₁-C₆₀heteroaryl group, a monovalent non-aromatic condensed polycyclic group,a monovalent non-aromatic condensed heteropolycyclic group, a biphenylgroup, and a terphenyl group, but embodiments of the present disclosureare not limited thereto.

In one embodiment, R₃ and R₁₁ to R₁₆ may each independently be selectedfrom hydrogen, deuterium, —F, —Cl, —Br, —I, a C₆-C₆₀ aryl group, and aC₁-C₆₀ heteroaryl group.

In one or more embodiments, R₃ and R₁₁ to R₁₆ may each independently beselected from:

hydrogen, deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group,a nitro group, an amidino group, a hydrazino group, a hydrazono group, amethyl group, an ethyl group, a propyl group, an isobutyl group, asec-butyl group, a ter-butyl group, a pentyl group, an iso-amyl group, ahexyl group, a phenyl group, a naphthyl group, a biphenyl group, aterphenyl group, a pyridyl group, a pyrimidyl group, a pyrazinyl group,a pyridazinyl group, a triazinyl group, a quinolinyl group, anisoquinolinyl group, a quinoxalinyl group, a quinazolinyl group, aphenanthrolinyl group, a pyrazolyl group, an imidazolyl group, atriazolyl group, an oxazolyl group, an isoxazolyl group, a thiazolylgroup, an isothiazolyl group, an oxadiazolyl group, a thiadiazolylgroup, a benzopyrazolyl group, a benzimidazolyl group, a benzoxazolylgroup, a benzothiazole group, a benzoxadiazole group, abenzothiadiazolyl group, a 5,6,7,8-tetrahydroisoquinolinyl group, a5,6,7,8-tetrahydroquinoline group, a carbazolyl group, a phenanthridinylgroup, an acridinyl group, a phenanthrolinyl group, a phenazinyl group,a triazinyl group, a dibenzofuranyl group, and a dibenzothiophenylgroup; and

a substituted methyl group, an ethyl group, a propyl group, an isobutylgroup, a sec-butyl group, a ter-butyl group, a pentyl group, an iso-amylgroup, a hexyl group, a phenyl group, a naphthyl group, a biphenylgroup, a terphenyl group, a pyridyl group, a pyrimidyl group, apyrazinyl group, a pyridazinyl group, a triazinyl group, a quinolinylgroup, an isoquinolinyl group, a quinoxalinyl group, a quinazolinylgroup, a phenanthrolinyl group, a pyrazolyl group, an imidazolyl group,a triazolyl group, an oxazolyl group, an isoxazolyl group, a thiazolylgroup, an isothiazolyl group, an oxadiazolyl group, a thiadiazolylgroup, a benzopyrazolyl group, a benzimidazolyl group, a benzoxazolylgroup, a benzothiazole group, a benzoxadiazole group, abenzothiadiazolyl group, a 5,6,7,8-tetrahydroisoquinolinyl group, a5,6,7,8-tetrahydroquinoline group, a carbazolyl group, a phenanthridinylgroup, an acridinyl group, a phenanthrolinyl group, a phenazinyl group,a triazinyl group, a dibenzofuranyl group, and a dibenzothiophenylgroup, each substituted with at least one selected from deuterium, —F,—Cl, —Br, —I, a hydroxyl group, a cyano group, a nitro group, an amidinogroup, a hydrazino group, a hydrazono group, a methyl group, an ethylgroup, a propyl group, an isobutyl group, a sec-butyl group, a ter-butylgroup, a pentyl group, an iso-amyl group, a hexyl group, a C₁-C₂₀ alkoxygroup, a cyclopentyl group, a cyclohexyl group, a cycloheptyl group, acyclopentenyl group, a cyclohexenyl group, a phenyl group, a naphthylgroup, a fluorenyl group, a pyridyl group, a pyrimidyl group, atriazinyl group, a quinolinyl group, an isoquinolinyl group, abenzoquinolinyl group, a naphthyridinyl group, a quinoxalinyl group, aquinazolinyl group, a carbazolyl group, a dibenzofuranyl group, abenzonaphthofuranyl group, a dibenzothiophenyl group, a benzocarbazolylgroup, and a dibenzocarbazolyl group,

but embodiments of the present disclosure are not limited thereto.

In one or more embodiments, R₃ and R₁₁ to R₁₆ may each independently beselected from:

hydrogen, deuterium, —F, —Cl, —Br, —I, a phenyl group, a naphthyl group,a biphenyl group, and a terphenyl group; and

a phenyl group, a naphthyl group, a biphenyl group, and a terphenylgroup, each substituted with at least one selected from deuterium, —F,—Cl, —Br, —I, a hydroxyl group, a cyano group, a nitro group, an amidinogroup, a hydrazino group, a hydrazono group, a methyl group, an ethylgroup, a propyl group, an isobutyl group, a sec-butyl group, a ter-butylgroup, a pentyl group, an iso-amyl group, a hexyl group, a C₁-C₂₀ alkoxygroup, a phenyl group, a naphthyl group, a fluorenyl group, a pyridylgroup, a pyrimidyl group, a triazinyl group, a quinolinyl group, anisoquinolinyl group, a benzoquinolinyl group, a naphthyridinyl group, aquinoxalinyl group, a quinazolinyl group, a carbazolyl group, adibenzofuranyl group, a benzonaphthofuranyl group, a dibenzothiophenylgroup, a benzocarbazolyl group, and a dibenzocarbazolyl group,

but embodiments of the present disclosure are not limited thereto.

In one embodiment, (i) c1 may be 1, and a moiety represented by

in Formula 2A or 2B may be represented by Formula 4A-1 or 4A-2:

In one or more embodiments, c2 may be 1, and a moiety represented by

in Formula 2A or 2B may be represented by Formula 4B-1 or 4B-2:

In Formulae 4A-1, 4A-2, 4B-1, and 4B-2,

Y₁₁, Y₁₂, Y₁₃, Y₂₁, Y₂₂, and Y₂₃ may each independently be N or C,

*and *′ each indicate a binding site to a neighboring atom, and

^(*1) and ^(*2) each indicate a binding site to M in Formula 1.

In one embodiment, c1 may be 1, and a moiety represented by

in Formula 2A or 2B may be represented by Formula 4A-1-1:

In one or more embodiments, (ii) c2 may be 1, and a moiety representedby

in Formula 2A or 2B may be represented by Formula 4B-1-1:

In Formulae 4A-1-1 and 4B-1-1,

Y₁₁, Y₁₂, Y₁₃, Y₂₁, Y₂₂, and Y₂₃ may each independently be N or C,

*and *′ each indicate a binding site to a neighboring atom, and

^(*1) and ^(*2) each indicate a binding site to M in Formula 1.

In one embodiment, Y₁₂ and Y₂₂ in Formulae 4A-1-1 and 4B-1-1 may each beC, but embodiments of the present disclosure are not limited thereto.

two neighboring groups selected from Y₁, Y₂, Y₃, Y₄, Y₁₁, Y₁₂, Y₁₃, Y₂₁,Y₂₂, and Y₂₃ in Formulae 4A-1, 4A-2, 4B-1, 4B-2, 4A-1-1, and 4B-1-1 maybe a single bond or a double bond.

In one embodiment, the organometallic compound may be selected fromCompounds 1 to 42, but embodiments of the present disclosure are notlimited thereto:

In general, an intermolecular aggregation easily occurs in a metalcomplex of a solid, for example, a d⁸ planar metal complex such asPt(II), due to a strong intermolecular interaction such as aligand-ligand, metal-metal, and/or ligand-metal interaction. Due to sucha phenomenon, when the degree of doping exceeds about 0.1%, which is thedegree often used in the art, it is highly likely that an aggregation ofcomplex units will be caused in an emission layer. Such aggregationcauses formation what is referred to as an excimer (also referred to asexciplex) at the time of optical and/or electrical excitation. Since theexcimer has a wide emission band without a regular system (e.g., theexcimer does not emit light having a narrow band of wavelengths in anordered system), it is difficult to implement pure basic colors (RGB)when the excimer is present.

In embodiments of the present disclosure, the ligand of theorganometallic compound represented by Formula 1 is always substitutedwith the substituent represented by Formula 3, and thus is oriented in away that an isoxazole or pyrazole substituent is perpendicular (e.g.,substantially perpendicular) to the substituent represented by Formula3. Therefore, as compared with the structure having no such substituent,steric hindrance occurs (or is increased) and the formation of anexcimer is hindered by intermolecular stacking. Thus, it is possible toimplement a light-emitting device having high efficiency and a longlifespan in a color region of deep blue light. For example, when theligand and the substituent represented by Formula 3 are linked via a C—Cbond, the effect of a distortion structure is increased and the effectof excimer formation suppression is increased (or maximized).

The organometallic compound according to embodiments of the presentdisclosure may emit blue light. For example, the organometallic compoundmay emit blue light having an upper (or a maximum) emission wavelengthof 440 nm to 495 nm, for example, 450 nm to 465 nm (in the case ofbottom emission, CIE_(x,y) color coordinates (0.14, 0.06) to (0.14,0.08)), but embodiments of the present disclosure are not limitedthereto. Accordingly, the organometallic compound represented by Formula1 may be suitably used to manufacture an organic light-emitting devicethat emits deep blue light.

A synthesis method for the organometallic compound represented byFormula 1 will be readily apparent to those of ordinary skill in the artby referring to the following examples.

At least one of the organometallic compound of Formula 1 may be usedbetween a pair of electrodes of an organic light-emitting device. Forexample, the organometallic compound may be included in an emissionlayer. The organometallic compound may act as a dopant in the emissionlayer.

Accordingly, provided is an organic light-emitting device including: afirst electrode; a second electrode facing the first electrode; and anorganic layer between the first electrode and the second electrode, theorganic layer including an emission layer, wherein the organic layerincludes at least one organometallic compound represented by Formula 1.

The expression “(an organic layer) includes at least one organometalliccompound” used herein may include a case in which “(an organic layer)includes identical compounds represented by Formula 1” and a case inwhich “(an organic layer) includes two or more different organometalliccompounds represented by Formula 1.”

For example, the organic layer may include, as the organometalliccompound, only Compound 1. In this regard, Compound 1 may exist in anemission layer of the organic light-emitting device. In one or moreembodiments, the organic layer may include, as the organometalliccompound, Compound 1 and Compound 2. In this regard, Compound 1 andCompound 2 may exist in an identical layer (for example, Compound 1 andCompound 2 may all exist in an emission layer), or different layers (forexample, Compound 1 may exist in an emission layer and Compound 2 mayexist in an electron transport region).

According to one embodiment,

the first electrode of the organic light-emitting device may be ananode,

the second electrode of the organic light-emitting device may be acathode,

the organic layer may further include a hole transport region betweenthe first electrode and the emission layer and an electron transportregion between the emission layer and the second electrode,

the hole transport region may include a hole injection layer, a holetransport layer, an emission auxiliary layer, an electron blockinglayer, or any combination thereof, and

the electron transport region may include a hole blocking layer, anelectron transport layer, an electron injection layer, or anycombination thereof.

The term “organic layer” as used herein refers to a single layer and/ora plurality of layers disposed between the first electrode and thesecond electrode of the organic light-emitting device. A materialincluded in the “organic layer” is not limited to an organic material.

Description of the Accompanying Drawing

The accompanying drawing is a schematic view of an organiclight-emitting device 10 according to an embodiment. The organiclight-emitting device 10 includes a first electrode 110, an organiclayer 150, and a second electrode 190.

Hereinafter, the structure of the organic light-emitting device 10according to an embodiment and a method of manufacturing the organiclight-emitting device 10 will be described in connection with theaccompanying drawing.

[First Electrode 110]

In the accompanying drawing, a substrate may be additionally disposedunder the first electrode 110 or above the second electrode 190. Thesubstrate may be a glass substrate or a plastic substrate, each havingexcellent mechanical strength, thermal stability, transparency, surfacesmoothness, ease of handling, and water resistance.

The first electrode 110 may be formed by depositing or sputtering amaterial for forming the first electrode 110 on the substrate. When thefirst electrode 110 is an anode, the material for a first electrode maybe selected from materials with a high work function to facilitate holeinjection.

The first electrode 110 may be a reflective electrode, asemi-transmissive electrode, or a transmissive electrode. When the firstelectrode 110 is a transmissive electrode, a material for forming afirst electrode may be selected from indium tin oxide (ITO), indium zincoxide (IZO), tin oxide (SnO₂), zinc oxide (ZnO), and any combinationsthereof, but embodiments of the present disclosure are not limitedthereto. In one or more embodiments, when the first electrode 110 is asemi-transmissive electrode or a reflectable electrode, a material forforming a first electrode may be selected from magnesium (Mg), silver(Ag), aluminum (Al), aluminum-lithium (Al—Li), calcium (Ca),magnesium-indium (Mg—In), magnesium-silver (Mg—Ag), and any combinationsthereof, but embodiments of the present disclosure are not limitedthereto.

The first electrode 110 may have a single-layered structure, or amulti-layered structure including two or more layers. For example, thefirst electrode 110 may have a three-layered structure of ITO/Ag/ITO,but the structure of the first electrode 110 is not limited thereto.

[Organic Layer 150]

The organic layer 150 is disposed on the first electrode 110. Theorganic layer 150 may include an emission layer.

The organic layer 150 may further include a hole transport regionbetween the first electrode 110 and the emission layer, and an electrontransport region between the emission layer and the second electrode190.

[Hole Transport Region in Organic Layer 150]

The hole transport region may have i) a single-layered structureincluding a single layer including a single material, ii) asingle-layered structure including a single layer including a pluralityof different materials, or iii) a multi-layered structure having aplurality of layers including a plurality of different materials.

The hole transport region may include at least one layer selected from ahole injection layer, a hole transport layer, an emission auxiliarylayer, and an electron blocking layer.

For example, the hole transport region may have a single-layeredstructure including a single layer including a plurality of differentmaterials, or a multi-layered structure having a hole injectionlayer/hole transport layer structure, a hole injection layer/holetransport layer/emission auxiliary layer structure, a hole injectionlayer/emission auxiliary layer structure, a hole transportlayer/emission auxiliary layer structure, or a hole injection layer/holetransport layer/electron blocking layer structure, wherein for eachstructure, constituting layers are sequentially stacked from the firstelectrode 110 in this stated order, but the structure of the holetransport region is not limited thereto.

The hole transport region may include at least one selected fromm-MTDATA, TDATA, 2-TNATA, NPB (NPD), β-NPB, TPD, Spiro-TPD, Spiro-NPB,methylated-NPB, TAPC, HMTPD, 4,4′,4″-tris(N-carbazolyl)triphenylamine(TCTA), polyaniline/dodecylbenzenesulfonic acid (PANI/DBSA),poly(3,4-ethylenedioxythiophene)/poly(4-styrenesulfonate) (PEDOT/PSS),polyaniline/camphor sulfonic acid (PANI/CSA),polyaniline/poly(4-styrenesulfonate) (PANI/PSS), a compound representedby Formula 201, and a compound represented by Formula 202:

In Formulae 201 and 202,

L₂₀₁ to L₂₀₄ may each independently be selected from a substituted orunsubstituted C₃-C₁₀ cycloalkylene group, a substituted or unsubstitutedC₁-C₁₀ heterocycloalkylene group, a substituted or unsubstituted C₃-C₁₀cycloalkenylene group, a substituted or unsubstituted C₁-C₁₀heterocycloalkenylene group, a substituted or unsubstituted C₆-C₆₀arylene group, a substituted or unsubstituted C₁-C₆₀ heteroarylenegroup, a substituted or unsubstituted divalent non-aromatic condensedpolycyclic group, and a substituted or unsubstituted divalentnon-aromatic condensed heteropolycyclic group,

L₂₀₅ may be selected from *—O—*′, *—S—*′, *—N(Q₂₀₁)-*′, a substituted orunsubstituted C₁-C₂₀ alkylene group, a substituted or unsubstitutedC₂-C₂₀ alkenylene group, a substituted or unsubstituted C₃-C₁₀cycloalkylene group, a substituted or unsubstituted C₁-C₁₀heterocycloalkylene group, a substituted or unsubstituted C₃-C₁₀cycloalkenylene group, a substituted or unsubstituted C₁-C₁₀heterocycloalkenylene group, a substituted or unsubstituted C₆-C₆₀arylene group, a substituted or unsubstituted C₁-C₆₀ heteroarylenegroup, a substituted or unsubstituted divalent non-aromatic condensedpolycyclic group, and a substituted or unsubstituted divalentnon-aromatic condensed heteropolycyclic group,

xa1 to xa4 may each independently be an integer from 0 to 3,

xa5 may be an integer from 1 to 10, and

R₂₀₁ to R₂₀₄ and Q₂₀₁ may each independently be selected from asubstituted or unsubstituted C₃-C₁₀ cycloalkyl group, a substituted orunsubstituted C₁-C₁₀ heterocycloalkyl group, a substituted orunsubstituted C₃-C₁₀ cycloalkenyl group, a substituted or unsubstitutedC₁-C₁₀ heterocycloalkenyl group, a substituted or unsubstituted C₆-C₆₀aryl group, a substituted or unsubstituted C₆-C₆₀ aryloxy group, asubstituted or unsubstituted C₆-C₆₀ arylthio group, a substituted orunsubstituted C₁-C₆₀ heteroaryl group, a substituted or unsubstitutedmonovalent non-aromatic condensed polycyclic group, and a substituted orunsubstituted monovalent non-aromatic condensed heteropolycyclic group.

For example, in Formula 202, R₂₀₁ and R₂₀₂ may optionally be linked viaa single bond, a dimethyl-methylene group, or a diphenyl-methylenegroup, and R₂₀₃ and R₂₀₄ may optionally be linked via a single bond, adimethyl-methylene group, or a diphenyl-methylene group.

In one embodiment, in Formulae 201 and 202,

L₂₀₁ to L₂₀₅ may each independently be selected from:

a phenylene group, a pentalenylene group, an indenylene group, anaphthylene group, an azulenylene group, a heptalenylene group, anindacenylene group, an acenaphthylene group, a fluorenylene group, aspiro-bifluorenylene group, a benzofluorenylene group, adibenzofluorenylene group, a phenalenylene group, a phenanthrenylenegroup, an anthracenylene group, a fluoranthenylene group, atriphenylenylene group, a pyrenylene group, a chrysenylene group, anaphthacenylene group, a picenylene group, a perylenylene group, apentaphenylene group, a hexacenylene group, a pentacenylene group, arubicenylene group, a coronenylene group, an ovalenylene group, athiophenylene group, a furanylene group, a carbazolylene group, anindolylene group, an isoindolylene group, a benzofuranylene group, abenzothiophenylene group, a dibenzofuranylene group, adibenzothiophenylene group, a benzocarbazolylene group, adibenzocarbazolylene group, a dibenzosilolylene group, and apyridinylene group; and

a phenylene group, a pentalenylene group, an indenylene group, anaphthylene group, an azulenylene group, a heptalenylene group, anindacenylene group, an acenaphthylene group, a fluorenylene group, aspiro-bifluorenylene group, a benzofluorenylene group, adibenzofluorenylene group, a phenalenylene group, a phenanthrenylenegroup, an anthracenylene group, a fluoranthenylene group, atriphenylenylene group, a pyrenylene group, a chrysenylene group, anaphthacenylene group, a picenylene group, a perylenylene group, apentaphenylene group, a hexacenylene group, a pentacenylene group, arubicenylene group, a coronenylene group, an ovalenylene group, athiophenylene group, a furanylene group, a carbazolylene group, anindolylene group, an isoindolylene group, a benzofuranylene group, abenzothiophenylene group, a dibenzofuranylene group, adibenzothiophenylene group, a benzocarbazolylene group, adibenzocarbazolylene group, a dibenzosilolylene group, and apyridinylene group, each substituted with at least one selected fromdeuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, a nitrogroup, an amidino group, a hydrazino group, a hydrazono group, a C₁-C₂₀alkyl group, a C₁-C₂₀ alkoxy group, a cyclopentyl group, a cyclohexylgroup, a cycloheptyl group, a cyclopentenyl group, a cyclohexenyl group,a phenyl group, a biphenyl group, a terphenyl group, a phenyl groupsubstituted with a C₁-C₁₀ alkyl group, a phenyl group substituted with—F, a pentalenyl group, an indenyl group, a naphthyl group, an azulenylgroup, a heptalenyl group, an indacenyl group, an acenaphthyl group, afluorenyl group, a spiro-bifluorenyl group, a benzofluorenyl group, adibenzofluorenyl group, a phenalenyl group, a phenanthrenyl group, ananthracenyl group, a fluoranthenyl group, a triphenylenyl group, apyrenyl group, a chrysenyl group, a naphthacenyl group, a picenyl group,a perylenyl group, a pentaphenyl group, a hexacenyl group, a pentacenylgroup, a rubicenyl group, a coronenyl group, an ovalenyl group, athiophenyl group, a furanyl group, a carbazolyl group, an indolyl group,an isoindolyl group, a benzofuranyl group, a benzothiophenyl group, adibenzofuranyl group, a dibenzothiophenyl group, a benzocarbazolylgroup, a dibenzocarbazolyl group, a dibenzosilolyl group, a pyridinylgroup, —Si(Q₃₁)(Q₃₂)(Q₃₃), and —N(Q₃₁)(Q₃₂), and

Q₃₁ to Q₃₃ may each independently be selected from a C₁-C₁₀ alkyl group,a C₁-C₁₀ alkoxy group, a phenyl group, a biphenyl group, a terphenylgroup, and a naphthyl group.

In one or more embodiments, xa1 to xa4 may each independently be 0, 1,or 2.

In one or more embodiments, xa5 may be 1, 2, 3, or 4.

In one or more embodiments, R₂₀₁ to R₂₀₄ and Q₂₀₁ may each independentlybe selected from:

a phenyl group, a biphenyl group, a terphenyl group, a pentalenyl group,an indenyl group, a naphthyl group, an azulenyl group, a heptalenylgroup, an indacenyl group, an acenaphthyl group, a fluorenyl group, aspiro-bifluorenyl group, a benzofluorenyl group, a dibenzofluorenylgroup, a phenalenyl group, a phenanthrenyl group, an anthracenyl group,a fluoranthenyl group, a triphenylenyl group, a pyrenyl group, achrysenyl group, a naphthacenyl group, a picenyl group, a perylenylgroup, a pentaphenyl group, a hexacenyl group, a pentacenyl group, arubicenyl group, a coronenyl group, an ovalenyl group, a thiophenylgroup, a furanyl group, a carbazolyl group, an indolyl group, anisoindolyl group, a benzofuranyl group, a benzothiophenyl group, adibenzofuranyl group, a dibenzothiophenyl group, a benzocarbazolylgroup, a dibenzocarbazolyl group, a dibenzosilolyl group, and apyridinyl group; and

a phenyl group, a biphenyl group, a terphenyl group, a pentalenyl group,an indenyl group, a naphthyl group, an azulenyl group, a heptalenylgroup, an indacenyl group, an acenaphthyl group, a fluorenyl group, aspiro-bifluorenyl group, a benzofluorenyl group, a dibenzofluorenylgroup, a phenalenyl group, a phenanthrenyl group, an anthracenyl group,a fluoranthenyl group, a triphenylenyl group, a pyrenyl group, achrysenyl group, a naphthacenyl group, a picenyl group, a perylenylgroup, a pentaphenyl group, a hexacenyl group, a pentacenyl group, arubicenyl group, a coronenyl group, an ovalenyl group, a thiophenylgroup, a furanyl group, a carbazolyl group, an indolyl group, anisoindolyl group, a benzofuranyl group, a benzothiophenyl group, adibenzofuranyl group, a dibenzothiophenyl group, a benzocarbazolylgroup, a dibenzocarbazolyl group, a dibenzosilolyl group, and apyridinyl group, each substituted with at least one selected fromdeuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, a nitrogroup, an amidino group, a hydrazino group, a hydrazono group, a C₁-C₂₀alkyl group, a C₁-C₂₀ alkoxy group, a cyclopentyl group, a cyclohexylgroup, a cycloheptyl group, a cyclopentenyl group, a cyclohexenyl group,a phenyl group, a biphenyl group, a terphenyl group, a phenyl groupsubstituted with a C₁-C₁₀ alkyl group, a phenyl group substituted with—F, a pentalenyl group, an indenyl group, a naphthyl group, an azulenylgroup, a heptalenyl group, an indacenyl group, an acenaphthyl group, afluorenyl group, a spiro-bifluorenyl group, a benzofluorenyl group, adibenzofluorenyl group, a phenalenyl group, a phenanthrenyl group, ananthracenyl group, a fluoranthenyl group, a triphenylenyl group, apyrenyl group, a chrysenyl group, a naphthacenyl group, a picenyl group,a perylenyl group, a pentaphenyl group, a hexacenyl group, a pentacenylgroup, a rubicenyl group, a coronenyl group, an ovalenyl group, athiophenyl group, a furanyl group, a carbazolyl group, an indolyl group,an isoindolyl group, a benzofuranyl group, a benzothiophenyl group, adibenzofuranyl group, a dibenzothiophenyl group, a benzocarbazolylgroup, a dibenzocarbazolyl group, a dibenzosilolyl group, a pyridinylgroup, —Si(Q₃₁)(Q₃₂)(Q₃₃), and —N(Q₃₁)(Q₃₂), and

Q₃₁ to Q₃₃ are the same as described above.

In one or more embodiments, at least one of R₂₀₁ to R₂₀₃ in Formula 201may each independently be selected from:

a fluorenyl group, a spiro-bifluorenyl group, a carbazolyl group, adibenzofuranyl group, and a dibenzothiophenyl group; and

a fluorenyl group, a spiro-bifluorenyl group, a carbazolyl group, adibenzofuranyl group, and a dibenzothiophenyl group, each substitutedwith at least one selected from deuterium, —F, —Cl, —Br, —I, a hydroxylgroup, a cyano group, a nitro group, an amidino group, a hydrazinogroup, a hydrazono group, a C₁-C₂₀ alkyl group, a C₁-C₂₀ alkoxy group, acyclopentyl group, a cyclohexyl group, a cycloheptyl group, acyclopentenyl group, a cyclohexenyl group, a phenyl group, a biphenylgroup, a terphenyl group, a phenyl group substituted with a C₁-C₁₀ alkylgroup, a phenyl group substituted with —F, a naphthyl group, a fluorenylgroup, a spiro-bifluorenyl group, a carbazolyl group, a dibenzofuranylgroup, and a dibenzothiophenyl group,

but embodiments of the present disclosure are not limited thereto.

In one or more embodiments, in Formula 202, i) R₂₀₁ and R₂₀₂ may belinked via a single bond, and/or ii) R₂₀₃ and R₂₀₄ may be linked via asingle bond.

In one or more embodiments, at least one of R₂₀₁ to R₂₀₄ in Formula 202may be selected from:

a carbazolyl group; and

a carbazolyl group substituted with at least one selected fromdeuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, a nitrogroup, an amidino group, a hydrazino group, a hydrazono group, a C₁-C₂₀alkyl group, a C₁-C₂₀ alkoxy group, a cyclopentyl group, a cyclohexylgroup, a cycloheptyl group, a cyclopentenyl group, a cyclohexenyl group,a phenyl group, a biphenyl group, a terphenyl group, a phenyl groupsubstituted with a C₁-C₁₀ alkyl group, a phenyl group substituted with—F, a naphthyl group, a fluorenyl group, a spiro-bifluorenyl group, acarbazolyl group, a dibenzofuranyl group, and a dibenzothiophenyl group,

but embodiments of the present disclosure are not limited thereto.

The compound represented by Formula 201 may be represented by Formula201A:

In one embodiment, the compound represented by Formula 201 may berepresented by Formula 201A(1) below, but embodiments of the presentdisclosure are not limited thereto:

In one embodiment, the compound represented by Formula 201 may berepresented by Formula 201A-1 below, but embodiments of the presentdisclosure are not limited thereto:

In one embodiment, the compound represented by Formula 202 may berepresented by Formula 202A:

In one embodiment, the compound represented by Formula 202 may berepresented by Formula 202A-1:

In Formulae 201A, 201A(1), 201A-1, 202A, and 202A-1,

L₂₀₁ to L₂₀₃, xa1 to xa3, xa5 and R₂₀₂ to R₂₀₄ are the same as describedabove,

R₂₁₁ and R₂₁₂ may be understood by referring to the description providedherein in connection with R₂₀₃,

R₂₁₃ to R₂₁₇ may each independently be selected from hydrogen,deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, a nitrogroup, an amidino group, a hydrazino group, a hydrazono group, a C₁-C₂₀alkyl group, a C₁-C₂₀ alkoxy group, a cyclopentyl group, a cyclohexylgroup, a cycloheptyl group, a cyclopentenyl group, a cyclohexenyl group,a phenyl group, a biphenyl group, a terphenyl group, a phenyl groupsubstituted with a C₁-C₁₀ alkyl group, a phenyl group substituted with—F, a pentalenyl group, an indenyl group, a naphthyl group, an azulenylgroup, a heptalenyl group, an indacenyl group, an acenaphthyl group, afluorenyl group, a spiro-bifluorenyl group, a benzofluorenyl group, adibenzofluorenyl group, a phenalenyl group, a phenanthrenyl group, ananthracenyl group, a fluoranthenyl group, a triphenylenyl group, apyrenyl group, a chrysenyl group, a naphthacenyl group, a picenyl group,a perylenyl group, a pentaphenyl group, a hexacenyl group, a pentacenylgroup, a rubicenyl group, a coronenyl group, an ovalenyl group, athiophenyl group, a furanyl group, a carbazolyl group, an indolyl group,an isoindolyl group, a benzofuranyl group, a benzothiophenyl group, adibenzofuranyl group, a dibenzothiophenyl group, a benzocarbazolylgroup, a dibenzocarbazolyl group, a dibenzosilolyl group, and apyridinyl group.

The hole transport region may include at least one compound selectedfrom Compounds HT1 to HT39, but embodiments of the present disclosureare not limited thereto:

A thickness of the hole transport region may be in a range of about 100Å to about 10,000 Å, for example, about 100 Å to about 1,000 Å. When thehole transport region includes at least one of a hole injection layerand a hole transport layer, a thickness of the hole injection layer maybe in a range of about 100 Å to about 9,000 Å, for example, about 100 Åto about 1,000 Å, and a thickness of the hole transport layer may be ina range of about 50 Å to about 2,000 Å, for example about 100 Å to about1,500 Å. When the thicknesses of the hole transport region, the holeinjection layer, and the hole transport layer are within these ranges,suitable or satisfactory hole transporting characteristics may beobtained without a substantial increase in driving voltage.

The emission auxiliary layer may increase light-emission efficiency bycompensating for an optical resonance distance according to thewavelength of light emitted by an emission layer, and the electronblocking layer may block the flow of electrons from an electrontransport region. The emission auxiliary layer and the electron blockinglayer may include the materials as described above.

[p-Dopant]

The hole transport region may further include, in addition to thesematerials, a charge-generation material for the improvement ofconductive properties. The charge-generation material may behomogeneously or non-homogeneously dispersed in the hole transportregion.

The charge-generation material may be, for example, a p-dopant.

In one embodiment, the p-dopant may have a lowest unoccupied molecularorbital of about −3.5 eV or less.

The p-dopant may include at least one selected from a quinonederivative, a metal oxide, and a cyano group-containing compound, butembodiments of the present disclosure are not limited thereto.

For example, the p-dopant may include at least one selected from:

a quinone derivative, such as tetracyanoquinodimethane (TCNQ) or2,3,5,6-tetrafluoro-7,7,8,8-tetracyanoquinodimethane (F4-TCNQ);

a metal oxide, such as tungsten oxide or molybdenum oxide;

1,4,5,8,9,11-hexaazatriphenylene-hexacarbonitrile (HAT-CN); and

a compound represented by Formula 221 below:

but embodiments of the present disclosure are not limited thereto:

In Formula 221,

R₂₂₁ to R₂₂₃ may each independently be selected from a substituted orunsubstituted C₃-C₁₀ cycloalkyl group, a substituted or unsubstitutedC₁-C₁₀ heterocycloalkyl group, a substituted or unsubstituted C₃-C₁₀cycloalkenyl group, a substituted or unsubstituted C₁-C₁₀heterocycloalkenyl group, a substituted or unsubstituted C₆-C₆₀ arylgroup, a substituted or unsubstituted C₁-C₆₀ heteroaryl group, asubstituted or unsubstituted monovalent non-aromatic condensedpolycyclic group, and a substituted or unsubstituted monovalentnon-aromatic condensed heteropolycyclic group, wherein at least oneselected from R₂₂₁ to R₂₂₃ may have at least one substituent selectedfrom a cyano group, —F, —Cl, —Br, —I, a C₁-C₂₀ alkyl group substitutedwith —F, a C₁-C₂₀ alkyl group substituted with —Cl, a C₁-C₂₀ alkyl groupsubstituted with —Br and a C₁-C₂₀ alkyl group substituted with —I.

[Emission Layer in Organic Layer 150]

When the organic light-emitting device 10 is a full-color organiclight-emitting device, the emission layer may be patterned into a redemission layer, a green emission layer, or a blue emission layer,according to a sub-pixel. In one or more embodiments, the emission layermay have a stacked structure of two or more layers selected from a redemission layer, a green emission layer, and a blue emission layer, inwhich the two or more layers contact each other or are separated fromeach other. In one or more embodiments, the emission layer may includetwo or more materials selected from a red light-emitting material, agreen light-emitting material, and a blue light-emitting material, inwhich the two or more materials are mixed with each other in a singlelayer to emit white light.

The emission layer may include a host and a dopant. The dopant mayinclude at least one selected from a phosphorescent dopant and afluorescent dopant.

An amount of the dopant in the emission layer may be, for example, in arange of about 0.01 parts by weight to about 15 parts by weight based on100 parts by weight of the host, but embodiments of the presentdisclosure are not limited thereto.

A thickness of the emission layer may be in a range of about 100 Å toabout 1,000 Å, for example, about 200 Å to about 600 Å. When thethickness of the emission layer is within this range, excellentlight-emission characteristics may be obtained without a substantialincrease in driving voltage.

[Host in Emission Layer]

In one or more embodiments, the host may include a compound representedby Formula 301 below.

[Ar₃₀₁]_(xb11)-[(L₃₀₁)_(xb1)-R₃₀₁]_(xb21).  Formula 301

In Formula 301,

Ar₃₀₁ may be a substituted or unsubstituted C₅-C₆₀ carbocyclic group ora substituted or unsubstituted C₁-C₆₀ heterocyclic group,

xb11 may be 1, 2, or 3,

L₃₀₁ may be selected from a substituted or unsubstituted C₃-C₁₀cycloalkylene group, a substituted or unsubstituted C₁-C₁₀heterocycloalkylene group, a substituted or unsubstituted C₃-C₁₀cycloalkenylene group, a substituted or unsubstituted C₁-C₁₀heterocycloalkenylene group, a substituted or unsubstituted C₆-C₆₀arylene group, a substituted or unsubstituted C₁-C₆₀ heteroarylenegroup, a substituted or unsubstituted divalent non-aromatic condensedpolycyclic group, and a substituted or unsubstituted divalentnon-aromatic condensed heteropolycyclic group,

xb1 may be an integer from 0 to 5,

R₃₀₁ may be selected from deuterium, —F, —Cl, —Br, —I, a hydroxyl group,a cyano group, a nitro group, an amidino group, a hydrazino group, ahydrazono group, a substituted or unsubstituted C₁-C₆₀ alkyl group, asubstituted or unsubstituted C₂-C₆₀ alkenyl group, a substituted orunsubstituted C₂-C₆₀ alkynyl group, a substituted or unsubstitutedC₁-C₆₀ alkoxy group, a substituted or unsubstituted C₃-C₁₀ cycloalkylgroup, a substituted or unsubstituted C₁-C₁₀ heterocycloalkyl group, asubstituted or unsubstituted C₃-C₁₀ cycloalkenyl group, a substituted orunsubstituted C₁-C₁₀ heterocycloalkenyl group, a substituted orunsubstituted C₆-C₆₀ aryl group, a substituted or unsubstituted C₆-C₆₀aryloxy group, a substituted or unsubstituted C₆-C₆₀ arylthio group, asubstituted or unsubstituted C₁-C₆₀ heteroaryl group, a substituted orunsubstituted monovalent non-aromatic condensed polycyclic group, asubstituted or unsubstituted monovalent non-aromatic condensedheteropolycyclic group, —Si(Q₃₀₁)(Q₃₀₂)(Q₃₀₃), —N(Q₃₀₁)(Q₃₀₂),—B(Q₃₀₁)(Q₃₀₂), —C(═O)(Q₃₀₁), —S(═O)₂(Q₃₀₁), and —P(═O)(Q₃₀₁)(Q₃₀₂),

xb21 may be an integer from 1 to 5, and

Q₃₀₁ to Q₃₀₃ may each independently be selected from a C₁-C₁₀ alkylgroup, a C₁-C₁₀ alkoxy group, a phenyl group, a biphenyl group, aterphenyl group, and a naphthyl group, but embodiments of the presentdisclosure are not limited thereto.

In one embodiment, Ar₃₀₁ in Formula 301 may be selected from:

a naphthalene group, a fluorene group, a spiro-bifluorene group, abenzofluorene group, a dibenzofluorene group, a phenalene group, aphenanthrene group, an anthracene group, a fluoranthene group, atriphenylene group, a pyrene group, a chrysene group, a naphthacenegroup, a picene group, a perylene group, a pentaphene group, anindenoanthracene group, a dibenzofuran group, and a dibenzothiophenegroup; and

a naphthalene group, a fluorene group, a spiro-bifluorene group, abenzofluorene group, a dibenzofluorene group, a phenalene group, aphenanthrene group, an anthracene group, a fluoranthene group, atriphenylene group, a pyrene group, a chrysene group, a naphthacenegroup, a picene group, a perylene group, a pentaphene group, anindenoanthracene group, a dibenzofuran group, and a dibenzothiophenegroup, each substituted with at least one selected from deuterium, —F,—Cl, —Br, —I, a hydroxyl group, a cyano group, a nitro group, an amidinogroup, a hydrazino group, a hydrazono group, a C₁-C₂₀ alkyl group, aC₁-C₂₀ alkoxy group, a phenyl group, a biphenyl group, a terphenylgroup, a naphthyl group, —Si(Q₃₁)(Q₃₂)(Q₃₃), —N(Q₃₁)(Q₃₂), —B(Q₃₁)(Q₃₂),—C(═O)(Q₃₁), —S(═O)₂(Q₃₁), and —P(═O)(Q₃₁)(Q₃₂), and

Q₃₁ to Q₃₃ may each independently be selected from a C₁-C₁₀ alkyl group,a C₁-C₁₀ alkoxy group, a phenyl group, a biphenyl group, a terphenylgroup, and a naphthyl group, but embodiments of the present disclosureare not limited thereto.

When xb11 in Formula 301 is two or more, two or more of Ar₃₀₁(s) may belinked via a single bond.

In one or more embodiments, the compound represented by Formula 301 maybe represented by Formula 301-1 or 301-2:

In Formulae 301-1 and 301-2,

A₃₀₁ to A₃₀₄ may each independently be selected from a benzene group, anaphthalene group, a phenanthrene group, a fluoranthene group, atriphenylene group, a pyrene group, a chrysene group, a pyridine group,a pyrimidine group, an indene group, a fluorene group, aspiro-bifluorene group, a benzofluorene group, a dibenzofluorene group,an indole group, a carbazole group, a benzocarbazole group, adibenzocarbazole group, a furan group, a benzofuran group, adibenzofuran group, a naphthofuran group, a benzonaphthofuran group, adinaphthofuran group, a thiophene group, a benzothiophene group, adibenzothiophene group, a naphthothiophene group, abenzonaphthothiophene group, and a dinaphthothiophene group,

X₃₀₁ may be O, S, or N-[(L₃₀₄)_(xb4)-R₃₀₄],

R₃₁₁ to R₃₁₄ may each independently be selected from hydrogen,deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, a nitrogroup, an amidino group, a hydrazino group, a hydrazono group, a C₁-C₂₀alkyl group, a C₁-C₂₀ alkoxy group, a phenyl group, a biphenyl group, aterphenyl group, a naphthyl group —Si(Q₃₁)(Q₃₂)(Q₃₃), —N(Q₃₁)(Q₃₂),—B(Q₃₁)(Q₃₂), —C(═O)(Q₃₁), —S(═O)₂(Q₃₁), and —P(═O)(Q₃₁)(Q₃₂),

xb22 and xb23 may each independently be 0, 1, or 2,

L₃₀₁, xb1, R₃₀₁, and Q₃₁ to Q₃₃ are the same as described above,

L₃₀₂ to L₃₀₄ may each independently be the same as described inconnection with L₃₀₁,

xb2 to xb4 may each independently be the same as described in connectionwith xb1, and

R₃₀₂ to R₃₀₄ may each independently be the same as described inconnection with R₃₀₁.

For example, in Formulae 301, 301-1, and 301-2, L₃₀₁ to L₃₀₄ may eachindependently be selected from:

a phenylene group, a naphthylene group, a fluorenylene group, aspiro-bifluorenylene group, a benzofluorenylene group, adibenzofluorenylene group, a phenanthrenylene group, an anthracenylenegroup, a fluoranthenylene group, a triphenylenylene group, a pyrenylenegroup, a chrysenylene group, a perylenylene group, a pentaphenylenegroup, a hexacenylene group, a pentacenylene group, a thiophenylenegroup, a furanylene group, a carbazolylene group, an indolylene group,an isoindolylene group, a benzofuranylene group, a benzothiophenylenegroup, a dibenzofuranylene group, a dibenzothiophenylene group, abenzocarbazolylene group, a dibenzocarbazolylene group, adibenzosilolylene group, a pyridinylene group, an imidazolylene group, apyrazolylene group, a thiazolylene group, an isothiazolylene group, anoxazolylene group, an isoxazolylene group, a thiadiazolylene group, anoxadiazolylene group, a pyrazinylene group, a pyrimidinylene group, apyridazinylene group, a triazinylene group, a quinolinylene group, anisoquinolinylene group, a benzoquinolinylene group, a phthalazinylenegroup, a naphthyridinylene group, a quinoxalinylene group, aquinazolinylene group, a cinnolinylene group, a phenanthridinylenegroup, an acridinylene group, a phenanthrolinylene group, aphenazinylene group, a benzimidazolylene group, an isobenzothiazolylenegroup, a benzoxazolylene group, an isobenzoxazolylene group, atriazolylene group, a tetrazolylene group, an imidazopyridinylene group,an imidazopyrimidinylene group, and an azacarbazolylene group; and

a phenylene group, a naphthylene group, a fluorenylene group, aspiro-bifluorenylene group, a benzofluorenylene group, adibenzofluorenylene group, a phenanthrenylene group, an anthracenylenegroup, a fluoranthenylene group, a triphenylenylene group, a pyrenylenegroup, a chrysenylene group, a perylenylene group, a pentaphenylenegroup, a hexacenylene group, a pentacenylene group, a thiophenylenegroup, a furanylene group, a carbazolylene group, an indolylene group,an isoindolylene group, a benzofuranylene group, a benzothiophenylenegroup, a dibenzofuranylene group, a dibenzothiophenylene group, abenzocarbazolylene group, a dibenzocarbazolylene group, adibenzosilolylene group, a pyridinylene group, an imidazolylene group, apyrazolylene group, a thiazolylene group, an isothiazolylene group, anoxazolylene group, an isoxazolylene group, a thiadiazolylene group, anoxadiazolylene group, a pyrazinylene group, a pyrimidinylene group, apyridazinylene group, a triazinylene group, a quinolinylene group, anisoquinolinylene group, a benzoquinolinylene group, a phthalazinylenegroup, a naphthyridinylene group, a quinoxalinylene group, aquinazolinylene group, a cinnolinylene group, a phenanthridinylenegroup, an acridinylene group, a phenanthrolinylene group, aphenazinylene group, a benzimidazolylene group, an isobenzothiazolylenegroup, a benzoxazolylene group, an isobenzoxazolylene group, atriazolylene group, a tetrazolylene group, an imidazopyridinylene group,an imidazopyrimidinylene group, and an azacarbazolylene group, eachsubstituted with at least one selected from deuterium, —F, —Cl, —Br, —I,a hydroxyl group, a cyano group, a nitro group, an amidino group, ahydrazino group, a hydrazono group, a C₁-C₂₀ alkyl group, a C₁-C₂₀alkoxy group, a phenyl group, a biphenyl group, a terphenyl group, anaphthyl group, a fluorenyl group, a spiro-bifluorenyl group, abenzofluorenyl group, a dibenzofluorenyl group, a phenanthrenyl group,an anthracenyl group, a fluoranthenyl group, a triphenylenyl group, apyrenyl group, a chrysenyl group, a perylenyl group, a pentaphenylgroup, a hexacenyl group, a pentacenyl group, a thiophenyl group, afuranyl group, a carbazolyl group, an indolyl group, an isoindolylgroup, a benzofuranyl group, a benzothiophenyl group, a dibenzofuranylgroup, a dibenzothiophenyl group, a benzocarbazolyl group, adibenzocarbazolyl group, a dibenzosilolyl group, a pyridinyl group, animidazolyl group, a pyrazolyl group, a thiazolyl group, an isothiazolylgroup, an oxazolyl group, an isoxazolyl group, a thiadiazolyl group, anoxadiazolyl group, a pyrazinyl group, a pyrimidinyl group, a pyridazinylgroup, a triazinyl group, a quinolinyl group, an isoquinolinyl group, abenzoquinolinyl group, a phthalazinyl group, a naphthyridinyl group, aquinoxalinyl group, a quinazolinyl group, a cinnolinyl group, aphenanthridinyl group, an acridinyl group, a phenanthrolinyl group, aphenazinyl group, a benzimidazolyl group, an isobenzothiazolyl group, abenzoxazolyl group, an isobenzoxazolyl group, a triazolyl group, atetrazolyl group, an imidazopyridinyl group, an imidazopyrimidinylgroup, an azacarbazolyl group, —Si(Q₃₁)(Q₃₂)(Q₃₃), —N(Q₃₁)(Q₃₂),—B(Q₃₁)(Q₃₂), —C(═O)(Q₃₁), —S(═O)₂(Q₃₁), and —P(═O)(Q₃₁)(Q₃₂), and

Q₃₁ to Q₃₃ are the same as described above.

In one embodiment, in Formulae 301, 301-1, and 301-2, R₃₀₁ to R₃₀₄ mayeach independently be selected from:

a phenyl group, a biphenyl group, a terphenyl group, a naphthyl group, afluorenyl group, a spiro-bifluorenyl group, a benzofluorenyl group, adibenzofluorenyl group, a phenanthrenyl group, an anthracenyl group, afluoranthenyl group, a triphenylenyl group, a pyrenyl group, a chrysenylgroup, a perylenyl group, a pentaphenyl group, a hexacenyl group, apentacenyl group, a thiophenyl group, a furanyl group, a carbazolylgroup, an indolyl group, an isoindolyl group, a benzofuranyl group, abenzothiophenyl group, a dibenzofuranyl group, a dibenzothiophenylgroup, a benzocarbazolyl group, a dibenzocarbazolyl group, adibenzosilolyl group, a pyridinyl group, an imidazolyl group, apyrazolyl group, a thiazolyl group, an isothiazolyl group, an oxazolylgroup, an isoxazolyl group, a thiadiazolyl group, an oxadiazolyl group,a pyrazinyl group, a pyrimidinyl group, a pyridazinyl group, a triazinylgroup, a quinolinyl group, an isoquinolinyl group, a benzoquinolinylgroup, a phthalazinyl group, a naphthyridinyl group, a quinoxalinylgroup, a quinazolinyl group, a cinnolinyl group, a phenanthridinylgroup, an acridinyl group, a phenanthrolinyl group, a phenazinyl group,a benzimidazolyl group, an isobenzothiazolyl group, a benzoxazolylgroup, an isobenzoxazolyl group, a triazolyl group, a tetrazolyl group,an imidazopyridinyl group, an imidazopyrimidinyl group, and anazacarbazolyl group; and

a phenyl group, a biphenyl group, a terphenyl group, a naphthyl group, afluorenyl group, a spiro-bifluorenyl group, a benzofluorenyl group, adibenzofluorenyl group, a phenanthrenyl group, an anthracenyl group, afluoranthenyl group, a triphenylenyl group, a pyrenyl group, a chrysenylgroup, a perylenyl group, a pentaphenyl group, a hexacenyl group, apentacenyl group, a thiophenyl group, a furanyl group, a carbazolylgroup, an indolyl group, an isoindolyl group, a benzofuranyl group, abenzothiophenyl group, a dibenzofuranyl group, a dibenzothiophenylgroup, a benzocarbazolyl group, a dibenzocarbazolyl group, adibenzosilolyl group, a pyridinyl group, an imidazolyl group, apyrazolyl group, a thiazolyl group, an isothiazolyl group, an oxazolylgroup, an isoxazolyl group, a thiadiazolyl group, an oxadiazolyl group,a pyrazinyl group, a pyrimidinyl group, a pyridazinyl group, a triazinylgroup, a quinolinyl group, an isoquinolinyl group, a benzoquinolinylgroup, a phthalazinyl group, a naphthyridinyl group, a quinoxalinylgroup, a quinazolinyl group, a cinnolinyl group, a phenanthridinylgroup, an acridinyl group, a phenanthrolinyl group, a phenazinyl group,a benzimidazolyl group, an isobenzothiazolyl group, a benzoxazolylgroup, an isobenzoxazolyl group, a triazolyl group, a tetrazolyl group,an imidazopyridinyl group, an imidazopyrimidinyl group, and anazacarbazolyl group, each substituted with at least one selected fromdeuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, a nitrogroup, an amidino group, a hydrazino group, a hydrazono group, a C₁-C₂₀alkyl group, a C₁-C₂₀ alkoxy group, a phenyl group, a biphenyl group, aterphenyl group, a naphthyl group, a fluorenyl group, aspiro-bifluorenyl group, a benzofluorenyl group, a dibenzofluorenylgroup, a phenanthrenyl group, an anthracenyl group, a fluoranthenylgroup, a triphenylenyl group, a pyrenyl group, a chrysenyl group, aperylenyl group, a pentaphenyl group, a hexacenyl group, a pentacenylgroup, a thiophenyl group, a furanyl group, a carbazolyl group, anindolyl group, an isoindolyl group, a benzofuranyl group, abenzothiophenyl group, a dibenzofuranyl group, a dibenzothiophenylgroup, a benzocarbazolyl group, a dibenzocarbazolyl group, adibenzosilolyl group, a pyridinyl group, an imidazolyl group, apyrazolyl group, a thiazolyl group, an isothiazolyl group, an oxazolylgroup, an isoxazolyl group, a thiadiazolyl group, an oxadiazolyl group,a pyrazinyl group, a pyrimidinyl group, a pyridazinyl group, a triazinylgroup, a quinolinyl group, an isoquinolinyl group, a benzoquinolinylgroup, a phthalazinyl group, a naphthyridinyl group, a quinoxalinylgroup, a quinazolinyl group, a cinnolinyl group, a phenanthridinylgroup, an acridinyl group, a phenanthrolinyl group, a phenazinyl group,a benzimidazolyl group, an isobenzothiazolyl group, a benzoxazolylgroup, an isobenzoxazolyl group, a triazolyl group, a tetrazolyl group,an imidazopyridinyl group, an imidazopyrimidinyl group, an azacarbazolylgroup, —Si(Q₃₁)(Q₃₂)(Q₃₃), —N(Q₃₁)(Q₃₂), —B(Q₃₁)(Q₃₂), —C(═O)(Q₃₁),—S(═O)₂(Q₃₁), and —P(═O)(Q₃₁)(Q₃₂), and

Q₃₁ to Q₃₃ are the same as described above.

In one or more embodiments, the host may include an alkaline earth metalcomplex. For example, the host may be selected from a Be complex (forexample, Compound H55), a Mg complex, and a Zn complex.

The host may include at least one selected from9,10-di(2-naphthyl)anthracene (ADN),2-methyl-9,10-bis(naphthalen-2-yl)anthracene (MADN),9,10-di-(2-naphthyl)-2-t-butyl-anthracene (TBADN),4,4′-bis(N-carbazolyl)-1,1′-biphenyl (CBP), 1,3-di-9-carbazolylbenzene(mCP), 1,3,5-tri(carbazol-9-yl)benzene (TCP), and Compounds H1 to H55,but embodiments of the present disclosure are not limited thereto:

In one embodiment, the host may include at least one selected from asilicon-containing compound (for example, BCPDS used in the followingexamples or the like) and a phosphine oxide-containing compound (forexample, POPCPA used in the following examples or the like).

However, embodiments of the present disclosure are not limited thereto.In one embodiment, the host may include only one compound, or two ormore different compounds (for example, a host used in the followingexamples includes BCPDS and POPCPA).

[Phosphorescent Dopant Included in Emission Layer in Organic Layer 150]

The phosphorescent dopant may include an organometallic compoundrepresented by Formula 1 below:

[Electron Transport Region in Organic Layer 150]

The electron transport region may have i) a single-layered structureincluding a single layer including a single material, ii) asingle-layered structure including a single layer including a pluralityof different materials, or iii) a multi-layered structure having aplurality of layers including a plurality of different materials.

The electron transport region may include at least one selected from abuffer layer, a hole blocking layer, an electron control layer, anelectron transport layer, and an electron injection layer, butembodiments of the present disclosure are not limited thereto.

For example, the electron transport region may have an electrontransport layer/electron injection layer structure, a hole blockinglayer/electron transport layer/electron injection layer structure, anelectron control layer/electron transport layer/electron injection layerstructure, or a buffer layer/electron transport layer/electron injectionlayer structure, wherein for each structure, constituting layers aresequentially stacked from an emission layer. However, embodiments of thestructure of the electron transport region are not limited thereto.

The electron transport region (for example, a buffer layer, a holeblocking layer, an electron control layer, or an electron transportlayer in the electron transport region) may include a metal-freecompound containing at least one π electron-depleted nitrogen-containingring.

The “π electron-depleted nitrogen-containing ring” indicates a C₁-C₆₀heterocyclic group having at least one *—N=*′ moiety as a ring-formingmoiety.

For example, the “π electron-depleted nitrogen-containing ring” may bei) a 60-membered to 7-membered heteromonocyclic group having at leastone *—N=*′ moiety, ii) a heteropolycyclic group in which two or more5-membered to 7-membered heteromonocyclic groups each having at leastone *—N=*′ moiety are condensed with each other (e.g., combinedtogether), or iii) a heteropolycyclic group in which at least one of5-membered to 7-membered heteromonocyclic groups, each having at leastone *—N=*′ moiety, is condensed with at least one C₅-C₆₀ carbocyclicgroup.

Examples of the π electron-depleted nitrogen-containing ring include animidazole, a pyrazole, a thiazole, an isothiazole, an oxazole, anisoxazole, a pyridine, a pyrazine, a pyrimidine, a pyridazine, anindazole, a purine, a quinoline, an isoquinoline, a benzoquinoline, aphthalazine, a naphthyridine, a quinoxaline, a quinazoline, a cinnoline,a phenanthridine, an acridine, a phenanthroline, a phenazine, abenzimidazole, an isobenzothiazole, a benzoxazole, an isobenzoxazole, atriazole, a tetrazole, an oxadiazole, a triazine, thiadiazole, animidazopyridine, an imidazopyrimidine, and an azacarbazole, but are notlimited thereto.

For example, the electron transport region may include a compoundrepresented by Formula 601:

Ar₆₀₁-[(L₆₀₁)_(xe1)-E₆₀₁]_(xe2).  Formula 601

In Formula 601,

Ar₆₀₁ may be a substituted or unsubstituted C₅-C₆₀ carbocyclic group ora substituted or unsubstituted C₁-C₆₀ heterocyclic group,

xe11 may be 1, 2, or 3,

L₆₀₁ may be selected from a substituted or unsubstituted C₃-C₁₀cycloalkylene group, a substituted or unsubstituted C₁-C₁₀heterocycloalkylene group, a substituted or unsubstituted C₃-C₁₀cycloalkenylene group, a substituted or unsubstituted C₁-C₁₀heterocycloalkenylene group, a substituted or unsubstituted C₆-C₆₀arylene group, a substituted or unsubstituted C₁-C₆₀ heteroarylenegroup, a substituted or unsubstituted divalent non-aromatic condensedpolycyclic group, and a substituted or unsubstituted divalentnon-aromatic condensed heteropolycyclic group,

xe1 may be an integer from 0 to 5,

R₆₀₁ may be selected from a substituted or unsubstituted C₃-C₁₀cycloalkyl group, a substituted or unsubstituted C₁-C₁₀ heterocycloalkylgroup, a substituted or unsubstituted C₃-C₁₀ cycloalkenyl group, asubstituted or unsubstituted C₁-C₁₀ heterocycloalkenyl group, asubstituted or unsubstituted C₆-C₆₀ aryl group, a substituted orunsubstituted C₆-C₆₀ aryloxy group, a substituted or unsubstitutedC₆-C₆₀ arylthio group, a substituted or unsubstituted C₁-C₆₀ heteroarylgroup, a substituted or unsubstituted monovalent non-aromatic condensedpolycyclic group, a substituted or unsubstituted monovalent non-aromaticcondensed heteropolycyclic group, —Si(Q₆₀₁)(Q₆₀₂)(Q₆₀₃), —C(═O)(Q₆₀₁),—S(═O)₂(Q₆₀₁), and —P(═O)(Q₆₀₁)(Q₆₀₂), and

Q₆₀₁ to Q₆₀₃ may each independently be a C₁-C₁₀ alkyl group, a C₁-C₁₀alkoxy group, a phenyl group, a biphenyl group, a terphenyl group, or anaphthyl group, and

xe21 may be an integer from 1 to 5.

In one embodiment, at least one of Ar₆₀₁(s) in the number of xe11 andR₆₀₁(s) in the number of xe21 may include the π electron-depletednitrogen-containing ring.

In one embodiment, in Formula 601, ring Ar₆₀₁ may be selected from:

a benzene group, a naphthalene group, a fluorene group, aspiro-bifluorene group, a benzofluorene group, a dibenzofluorene group,a phenalene group, a phenanthrene group, an anthracene group, afluoranthene group, a triphenylene group, a pyrene group, a chrysenegroup, a naphthacene group, a picene group, a perylene group, apentaphene group, an indenoanthracene group, a dibenzofuran group, adibenzothiophene group, a carbazole group, an imidazole group, apyrazole group, a thiazole group, an isothiazole group, an oxazolegroup, an isoxazole group, a pyridine group, a pyrazine group, apyrimidine group, a pyridazine group, an indazole group, a purine group,a quinoline group, an isoquinoline group, a benzoquinoline group, aphthalazine group, a naphthyridine group, a quinoxaline group, aquinazoline group, a cinnoline group, a phenanthridine group, anacridine group, a phenanthroline group, phenazine group, a benzimidazolegroup, an iso-benzothiazole group, a benzoxazole group, anisobenzoxazole group, a triazole group, a tetrazole group, an oxadiazolegroup, a triazine group, a thiadiazol group, an imidazopyridine group,an imidazopyrimidine group, and an azacarbazole group; and

a benzene group, a naphthalene group, a fluorene group, aspiro-bifluorene group, a benzofluorene group, a dibenzofluorene group,a phenalene group, a phenanthrene group, an anthracene group, afluoranthene group, a triphenylene group, a pyrene group, a chrysenegroup, a naphthacene group, a picene group, a perylene group, apentaphene group, an indenoanthracene group, a dibenzofuran group, adibenzothiophene group, a carbazole group, an imidazole group, apyrazole group, a thiazole group, an isothiazole group, an oxazolegroup, an isoxazole group, a pyridine group, a pyrazine group, apyrimidine group, a pyridazine group, an indazole group, a purine group,a quinoline group, an isoquinoline group, a benzoquinoline group, aphthalazine group, a naphthyridine group, a quinoxaline group, aquinazoline group, a cinnoline group, a phenanthridine group, anacridine group, a phenanthroline group, phenazine group, a benzimidazolegroup, an iso-benzothiazole group, a benzoxazole group, anisobenzoxazole group, a triazole group, a tetrazole group, an oxadiazolegroup, a triazine group, a thiadiazol group, an imidazopyridine group,an imidazopyrimidine group, and an azacarbazole group, each substitutedwith at least one selected from deuterium, —F, —Cl, —Br, —I, a hydroxylgroup, a cyano group, a nitro group, an amidino group, a hydrazinogroup, a hydrazono group, a C₁-C₂₀ alkyl group, a C₁-C₂₀ alkoxy group, aphenyl group, a biphenyl group, a terphenyl group, a naphthyl group,—Si(Q₃₁)(Q₃₂)(Q₃₃), —S(═O)₂(Q₃₁), and —P(═O)(Q₃₁)(Q₃₂), and

Q₃₁ to Q₃₃ may each independently be selected from a C₁-C₁₀ alkyl group,a C₁-C₁₀ alkoxy group, a phenyl group, a biphenyl group, a terphenylgroup, and a naphthyl group.

When xe11 in Formula 601 is two or more, two or more Ar601(s) may belinked via a single bond.

In one or more embodiments, Ar₆₀₁ in Formula 601 may be an anthracenegroup.

In one or more embodiments, a compound represented by Formula 601 may berepresented by Formula 601-1:

In Formula 601-1,

X₆₁₄ may be N or C(R₆₁₄), X₆₁₅ may be N or C(R₆₁₅), and X₆₁₆ may be N orC(R₆₁₆), wherein at least one selected from X₆₁₄ to X₆₁₆ may be N,

L₆₁₁ to L₆₁₃ may each independently be the same as described inconnection with L₆₀₁,

xe611 to xe613 may each independently be the same as described inconnection with xe1,

R₆₁₁ to R₆₁₃ may each independently be the same as described inconnection with R₆₀₁, and

R₆₁₄ to R₆₁₆ may each independently be selected from hydrogen,deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, a nitrogroup, an amidino group, a hydrazino group, a hydrazono group, a C₁-C₂₀alkyl group, a C₁-C₂₀ alkoxy group, a phenyl group, a biphenyl group, aterphenyl group, and a naphthyl group.

In one embodiment, in Formulae 601 and 601-1, L₆₀₁ and L₆₁₁ to L₆₁₃ mayeach independently be selected from:

a phenylene group, a naphthylene group, a fluorenylene group, aspiro-bifluorenylene group, a benzofluorenylene group, adibenzofluorenylene group, a phenanthrenylene group, an anthracenylenegroup, a fluoranthenylene group, a triphenylenylene group, a pyrenylenegroup, a chrysenylene group, a perylenylene group, a pentaphenylenegroup, a hexacenylene group, a pentacenylene group, a thiophenylenegroup, a furanylene group, a carbazolylene group, an indolylene group,an isoindolylene group, a benzofuranylene group, a benzothiophenylenegroup, a dibenzofuranylene group, a dibenzothiophenylene group, abenzocarbazolylene group, a dibenzocarbazolylene group, adibenzosilolylene group, a pyridinylene group, an imidazolylene group, apyrazolylene group, a thiazolylene group, an isothiazolylene group, anoxazolylene group, an isoxazolylene group, a thiadiazolylene group, anoxadiazolylene group, a pyrazinylene group, a pyrimidinylene group, apyridazinylene group, a triazinylene group, a quinolinylene group, anisoquinolinylene group, a benzoquinolinylene group, a phthalazinylenegroup, a naphthyridinylene group, a quinoxalinylene group, aquinazolinylene group, a cinnolinylene group, a phenanthridinylenegroup, an acridinylene group, a phenanthrolinylene group, aphenazinylene group, a benzimidazolylene group, an isobenzothiazolylenegroup, a benzoxazolylene group, an isobenzoxazolylene group, atriazolylene group, a tetrazolylene group, an imidazopyridinylene group,an imidazopyrimidinylene group, and an azacarbazolylene group; and

a phenylene group, a naphthylene group, a fluorenylene group, aspiro-bifluorenylene group, a benzofluorenylene group, adibenzofluorenylene group, a phenanthrenylene group, an anthracenylenegroup, a fluoranthenylene group, a triphenylenylene group, a pyrenylenegroup, a chrysenylene group, a perylenylene group, a pentaphenylenegroup, a hexacenylene group, a pentacenylene group, a thiophenylenegroup, a furanylene group, a carbazolylene group, an indolylene group,an isoindolylene group, a benzofuranylene group, a benzothiophenylenegroup, a dibenzofuranylene group, a dibenzothiophenylene group, abenzocarbazolylene group, a dibenzocarbazolylene group, adibenzosilolylene group, a pyridinylene group, an imidazolylene group, apyrazolylene group, a thiazolylene group, an isothiazolylene group, anoxazolylene group, an isoxazolylene group, a thiadiazolylene group, anoxadiazolylene group, a pyrazinylene group, a pyrimidinylene group, apyridazinylene group, a triazinylene group, a quinolinylene group, anisoquinolinylene group, a benzoquinolinylene group, a phthalazinylenegroup, a naphthyridinylene group, a quinoxalinylene group, aquinazolinylene group, a cinnolinylene group, a phenanthridinylenegroup, an acridinylene group, a phenanthrolinylene group, aphenazinylene group, a benzimidazolylene group, an isobenzothiazolylenegroup, a benzoxazolylene group, an isobenzoxazolylene group, atriazolylene group, a tetrazolylene group, an imidazopyridinylene group,an imidazopyrimidinylene group, and an azacarbazolylene group, eachsubstituted with at least one selected from deuterium, —F, —Cl, —Br, —I,a hydroxyl group, a cyano group, a nitro group, an amidino group, ahydrazino group, a hydrazono group, a C₁-C₂₀ alkyl group, a C₁-C₂₀alkoxy group, a phenyl group, a biphenyl group, a terphenyl group, anaphthyl group, a fluorenyl group, a spiro-bifluorenyl group, abenzofluorenyl group, a dibenzofluorenyl group, a phenanthrenyl group,an anthracenyl group, a fluoranthenyl group, a triphenylenyl group, apyrenyl group, a chrysenyl group, a perylenyl group, a pentaphenylgroup, a hexacenyl group, a pentacenyl group, a thiophenyl group, afuranyl group, a carbazolyl group, an indolyl group, an isoindolylgroup, a benzofuranyl group, a benzothiophenyl group, a dibenzofuranylgroup, a dibenzothiophenyl group, a benzocarbazolyl group, adibenzocarbazolyl group, a dibenzosilolyl group, a pyridinyl group, animidazolyl group, a pyrazolyl group, a thiazolyl group, an isothiazolylgroup, an oxazolyl group, an isoxazolyl group, a thiadiazolyl group, anoxadiazolyl group, a pyrazinyl group, a pyrimidinyl group, a pyridazinylgroup, a triazinyl group, a quinolinyl group, an isoquinolinyl group, abenzoquinolinyl group, a phthalazinyl group, a naphthyridinyl group, aquinoxalinyl group, a quinazolinyl group, a cinnolinyl group, aphenanthridinyl group, an acridinyl group, a phenanthrolinyl group, aphenazinyl group, a benzimidazolyl group, an isobenzothiazolyl group, abenzoxazolyl group, an isobenzoxazolyl group, a triazolyl group, atetrazolyl group, an imidazopyridinyl group, an imidazopyrimidinylgroup, and an azacarbazolyl group,

but embodiments of the present disclosure are not limited thereto.

In one or more embodiments, xe1 and xe611 to xe613 in Formulae 601 and601-1 may each independently be 0, 1, or 2.

In one or more embodiments, in Formulae 601 and 601-1, R₆₀₁ and R₆₁₁ toR₆₁₃ may each independently be selected from:

a phenyl group, a biphenyl group, a terphenyl group, a naphthyl group, afluorenyl group, a spiro-bifluorenyl group, a benzofluorenyl group, adibenzofluorenyl group, a phenanthrenyl group, an anthracenyl group, afluoranthenyl group, a triphenylenyl group, a pyrenyl group, a chrysenylgroup, a perylenyl group, a pentaphenyl group, a hexacenyl group, apentacenyl group, a thiophenyl group, a furanyl group, a carbazolylgroup, an indolyl group, an isoindolyl group, a benzofuranyl group, abenzothiophenyl group, a dibenzofuranyl group, a dibenzothiophenylgroup, a benzocarbazolyl group, a dibenzocarbazolyl group, adibenzosilolyl group, a pyridinyl group, an imidazolyl group, apyrazolyl group, a thiazolyl group, an isothiazolyl group, an oxazolylgroup, an isoxazolyl group, a thiadiazolyl group, an oxadiazolyl group,a pyrazinyl group, a pyrimidinyl group, a pyridazinyl group, a triazinylgroup, a quinolinyl group, an isoquinolinyl group, a benzoquinolinylgroup, a phthalazinyl group, a naphthyridinyl group, a quinoxalinylgroup, a quinazolinyl group, a cinnolinyl group, a phenanthridinylgroup, an acridinyl group, a phenanthrolinyl group, a phenazinyl group,a benzimidazolyl group, an isobenzothiazolyl group, a benzoxazolylgroup, an isobenzoxazolyl group, a triazolyl group, a tetrazolyl group,an imidazopyridinyl group, an imidazopyrimidinyl group, and anazacarbazolyl group;

a phenyl group, a biphenyl group, a terphenyl group, a naphthyl group, afluorenyl group, a spiro-bifluorenyl group, a benzofluorenyl group, adibenzofluorenyl group, a phenanthrenyl group, an anthracenyl group, afluoranthenyl group, a triphenylenyl group, a pyrenyl group, a chrysenylgroup, a perylenyl group, a pentaphenyl group, a hexacenyl group, apentacenyl group, a thiophenyl group, a furanyl group, a carbazolylgroup, an indolyl group, an isoindolyl group, a benzofuranyl group, abenzothiophenyl group, a dibenzofuranyl group, a dibenzothiophenylgroup, a benzocarbazolyl group, a dibenzocarbazolyl group, adibenzosilolyl group, a pyridinyl group, an imidazolyl group, apyrazolyl group, a thiazolyl group, an isothiazolyl group, an oxazolylgroup, an isoxazolyl group, a thiadiazolyl group, an oxadiazolyl group,a pyrazinyl group, a pyrimidinyl group, a pyridazinyl group, a triazinylgroup, a quinolinyl group, an isoquinolinyl group, a benzoquinolinylgroup, a phthalazinyl group, a naphthyridinyl group, a quinoxalinylgroup, a quinazolinyl group, a cinnolinyl group, a phenanthridinylgroup, an acridinyl group, a phenanthrolinyl group, a phenazinyl group,a benzimidazolyl group, an isobenzothiazolyl group, a benzoxazolylgroup, an isobenzoxazolyl group, a triazolyl group, a tetrazolyl group,an imidazopyridinyl group, an imidazopyrimidinyl group, and anazacarbazolyl group, each substituted with at least one selected fromdeuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, a nitrogroup, an amidino group, a hydrazino group, a hydrazono group, a C₁-C₂₀alkyl group, a C₁-C₂₀ alkoxy group, a phenyl group, a biphenyl group, aterphenyl group, a naphthyl group, a fluorenyl group, aspiro-bifluorenyl group, a benzofluorenyl group, a dibenzofluorenylgroup, a phenanthrenyl group, an anthracenyl group, a fluoranthenylgroup, a triphenylenyl group, a pyrenyl group, a chrysenyl group, aperylenyl group, a pentaphenyl group, a hexacenyl group, a pentacenylgroup, a thiophenyl group, a furanyl group, a carbazolyl group, anindolyl group, an isoindolyl group, a benzofuranyl group, abenzothiophenyl group, a dibenzofuranyl group, a dibenzothiophenylgroup, a benzocarbazolyl group, a dibenzocarbazolyl group, adibenzosilolyl group, a pyridinyl group, an imidazolyl group, apyrazolyl group, a thiazolyl group, an isothiazolyl group, an oxazolylgroup, an isoxazolyl group, a thiadiazolyl group, an oxadiazolyl group,a pyrazinyl group, a pyrimidinyl group, a pyridazinyl group, a triazinylgroup, a quinolinyl group, an isoquinolinyl group, a benzoquinolinylgroup, a phthalazinyl group, a naphthyridinyl group, a quinoxalinylgroup, a quinazolinyl group, a cinnolinyl group, a phenanthridinylgroup, an acridinyl group, a phenanthrolinyl group, a phenazinyl group,a benzimidazolyl group, an isobenzothiazolyl group, a benzoxazolylgroup, an isobenzoxazolyl group, a triazolyl group, a tetrazolyl group,an imidazopyridinyl group, an imidazopyrimidinyl group, and anazacarbazolyl group; and

—S(═O)₂(Q₆₀₁), and —P(═O)(Q₆₀₁)(Q₆₀₂), and

Q₆₀₁ and Q₆₀₂ are the same as described above.

The electron transport region may include at least one compound selectedfrom Compounds ET1 to ET36, but embodiments of the present disclosureare not limited thereto:

In one or more embodiments, the electron transport region may include atleast one compound selected from2,9-dimethyl-4,7-diphenyl-1,10-phenanthroline (BCP),4,7-diphenyl-1,10-phenanthroline (Bphen), Alq₃, BAIq,3-(biphenyl-4-yl)-5-(4-tert-butylphenyl)-4-phenyl-4H-1,2,4-triazole(TAZ),and NTAZ:

In one embodiment, the electron transport region may include a phosphineoxide-containing compound (for example, TSPO1 used in the followingexamples or the like), but embodiments of the present disclosure are notlimited thereto. In one embodiment, the phosphine oxide-containingcompound may be used in a hole blocking layer in the electron transportregion, but embodiments of the present disclosure are not limitedthereto.

A thickness of the buffer layer, the hole blocking layer, and/or theelectron control layer may be in a range of about 20 Å to about 1,000 Å,for example, about 30 Å to about 300 Å. When the thicknesses of thebuffer layer, the hole blocking layer, and/or the electron control layerare within these ranges, the electron blocking layer may have excellentelectron blocking characteristics or electron control characteristicswithout a substantial increase in driving voltage.

A thickness of the electron transport layer may be in a range of about100 Å to about 1,000 Å, for example, about 150 Å to about 500 Å. Whenthe thickness of the electron transport layer is within the rangedescribed above, the electron transport layer may have suitable orsatisfactory electron transport characteristics without a substantialincrease in driving voltage.

The electron transport region (for example, the electron transport layerin the electron transport region) may further include, in addition tothe materials described above, a metal-containing material.

The metal-containing material may include at least one selected fromalkali metal complex and alkaline earth-metal complex. The alkali metalcomplex may include a metal ion selected from a Li ion, a Na ion, a Kion, a Rb ion, and a Cs ion, and the alkaline earth-metal complex mayinclude a metal ion selected from a Be ion, a Mg ion, a Ca ion, a Srion, and a Ba ion. A ligand coordinated with the metal ion of the alkalimetal complex or the alkaline earth-metal complex may be selected from ahydroxy quinoline, a hydroxy isoquinoline, a hydroxy benzoquinoline, ahydroxy acridine, a hydroxy phenanthridine, a hydroxy phenyloxazole, ahydroxy phenylthiazole, a hydroxy diphenyloxadiazole, a hydroxydiphenylthiadiazole, a hydroxy phenylpyridine, a hydroxyphenylbenzimidazole, a hydroxy phenylbenzothiazole, a bipyridine, aphenanthroline, and a cyclopentadiene, but embodiments of the presentdisclosure are not limited thereto.

For example, the metal-containing material may include a Li complex. TheLi complex may include, for example, Compound ET-D1 (lithium quinolate,LiQ) and/or ET-D2:

The electron transport region may include an electron injection layerthat facilitates injection of electrons from the second electrode 190.The electron injection layer may directly contact the second electrode190.

The electron injection layer may have i) a single-layered structureincluding a single layer including a single material, ii) asingle-layered structure including a single layer including a pluralityof different materials, or iii) a multi-layered structure having aplurality of layers including a plurality of different materials.

The electron injection layer may include an alkali metal, an alkalineearth metal, a rare earth metal, an alkali metal compound, an alkalineearth-metal compound, a rare earth metal compound, an alkali metalcomplex, an alkaline earth-metal complex, a rare earth metal complex, orany combinations thereof.

The alkali metal may be selected from Li, Na, K, Rb, and Cs. In oneembodiment, the alkali metal may be Li, a Na, or Cs. In one or moreembodiments, the alkali metal may be Li or Cs, but embodiments of thepresent disclosure are not limited thereto.

The alkaline earth metal may be selected from Mg, Ca, Sr, and Ba.

The rare earth metal may be selected from Sc, Y, Ce, Tb, Yb, and Gd.

The alkali metal compound, the alkaline earth-metal compound, and therare earth metal compound may be selected from oxides and halides (forexample, fluorides, chlorides, bromides, or iodides) of the alkalimetal, the alkaline earth-metal, and the rare earth metal.

The alkali metal compound may be selected from alkali metal oxides, suchas Li₂O, Cs₂O, or K₂O, and alkali metal halides, such as LiF, NaF, CsF,KF, LiI, NaI, CsI, or KI. In one embodiment, the alkali metal compoundmay be selected from LiF, Li₂O, NaF, LiI, NaI, CsI, and KI, butembodiments of the present disclosure are not limited thereto.

The alkaline earth-metal compound may be selected from alkalineearth-metal oxides, such as BaO, SrO, CaO, Ba_(x)Sr_(1-x)O (0<x<1), orBa_(x)Ca_(1-x)O (0<x<1). In one embodiment, the alkaline earth-metalcompound may be selected from BaO, SrO, and CaO, but embodiments of thepresent disclosure are not limited thereto.

The rare earth metal compound may be selected from YbF₃, ScF₃, ScO₃,Y₂O₃, Ce₂O₃, GdF₃, and TbF₃. In one embodiment, the rare earth metalcompound may be selected from YbF3, ScF₃, TbF₃, Ybl₃, Scl₃, and Tbl₃,but embodiments of the present disclosure are not limited thereto.

The alkali metal complex, the alkaline earth-metal complex, and the rareearth metal complex may include an ion of alkali metal, alkalineearth-metal, and rare earth metal as described above, and a ligandcoordinated with a metal ion of the alkali metal complex, the alkalineearth-metal complex, or the rare earth metal complex may be selectedfrom hydroxy quinoline, hydroxy isoquinoline, hydroxy benzoquinoline,hydroxy acridine, hydroxy phenanthridine, hydroxy phenyloxazole, hydroxyphenylthiazole, hydroxy diphenyloxadiazole, hydroxy diphenylthiadiazole,hydroxy phenylpyridine, hydroxy phenylbenzimidazole, hydroxyphenylbenzothiazole, bipyridine, phenanthroline, and cyclopentadiene,but embodiments of the present disclosure are not limited thereto.

The electron injection layer may include (or consist of) an alkalimetal, an alkaline earth metal, a rare earth metal, an alkali metalcompound, an alkaline earth-metal compound, a rare earth metal compound,an alkali metal complex, an alkaline earth-metal complex, a rare earthmetal complex, or any combinations thereof, as described above. In oneor more embodiments, the electron injection layer may further include anorganic material. When the electron injection layer further includes anorganic material, an alkali metal, an alkaline earth metal, a rare earthmetal, an alkali metal compound, an alkaline earth-metal compound, arare earth metal compound, an alkali metal complex, an alkalineearth-metal complex, a rare earth metal complex, or any combinationsthereof may be homogeneously or non-homogeneously dispersed in a matrixincluding the organic material.

A thickness of the electron injection layer may be in a range of about 1Å to about 100 Å, for example, about 3 Å to about 90 Å. When thethickness of the electron injection layer is within the range describedabove, the electron injection layer may have suitable or satisfactoryelectron injection characteristics without a substantial increase indriving voltage.

[Second Electrode 190]

The second electrode 190 may be disposed on the organic layer 150 havingsuch a structure. The second electrode 190 may be a cathode which is anelectron injection electrode, and in this regard, a material for formingthe second electrode 190 may be selected from metal, an alloy, anelectrically conductive compound, and a combination thereof, which havea relatively low work function.

The second electrode 190 may include at least one selected from lithium(Li), silver (Ag), magnesium (Mg), aluminum (Al), aluminum-lithium(Al—Li), calcium (Ca), magnesium-indium (Mg—In), magnesium-silver(Mg—Ag), ITO, and IZO, but embodiments of the present disclosure are notlimited thereto. The second electrode 190 may be a transmissiveelectrode, a semi-transmissive electrode, or a reflective electrode.

The second electrode 190 may have a single-layered structure, or amulti-layered structure including two or more layers.

Layers constituting the hole transport region, an emission layer, andlayers constituting the electron transport region may be formed in acertain region by using one or more suitable methods selected fromvacuum deposition, spin coating, casting, Langmuir-Blodgett (LB)deposition, ink-jet printing, laser-printing, and laser-induced thermalimaging.

When layers constituting the hole transport region, an emission layer,and layers constituting the electron transport region may be formed byvacuum deposition, the vacuum deposition may be performed at adeposition temperature of about 100° C. to about 500° C., at a vacuumdegree of about 10⁻⁸ torr to about 10⁻³ torr, and at a deposition speedof about 0.01 Å/sec to about 100 Å/sec by taking into account a materialto be included in a layer to be formed, and the structure of a layer tobe formed.

When layers constituting the hole transport region, an emission layer,and layers constituting the electron transport region are formed by spincoating, the spin coating may be performed at a coating speed of about2,000 rpm to about 5,000 rpm and at a heat treatment temperature ofabout 80° C. to about 200° C. by taking into account a material to beincluded in a layer to be formed, and the structure of a layer to beformed.

[General Definitions of Substituents]

The term “C₁-C₆₀ alkyl group” as used herein refers to a linear orbranched aliphatic saturated hydrocarbon monovalent group having 1 to 60carbon atoms, and examples thereof include a methyl group, an ethylgroup, a propyl group, an isobutyl group, a sec-butyl group, atert-butyl group, a pentyl group, an iso-amyl group, and a hexyl group.The term “C₁-C₆₀ alkylene group” as used herein refers to a divalentgroup having substantially the same structure as the C₁-C₆₀ alkyl group,except that the C₁-C₆₀ alkylene group is divalent.

The term “C₂-C₆₀ alkenyl group” as used herein refers to a hydrocarbongroup having at least one carbon-carbon double bond in a main chain(e.g., the middle) or at the terminus of the C₂-C₆₀ alkyl group, andexamples thereof include an ethenyl group, a propenyl group, and abutenyl group. The term “C₂-C₆₀ alkenylene group” as used herein refersto a divalent group having substantially the same structure as theC₂-C₆₀ alkenyl group, except that the C₂-C₆₀ alkenylene group isdivalent.

The term “C₂-C₆₀ alkynyl group” as used herein refers to a hydrocarbongroup having at least one carbon-carbon triple bond in the middle or atthe terminus of the C₂-C₆₀ alkyl group, and examples thereof include anethynyl group, and a propynyl group. The term “C₂-C₆₀ alkynylene group”as used herein refers to a divalent group having substantially the samestructure as the C₂-C₆₀ alkynyl group, except that the C₂-C₆₀ alkynylenegroup is divalent.

The term “C₁-C₆₀ alkoxy group” as used herein refers to a monovalentgroup represented by —OA₁₀₁ (wherein A₁₀₁ is the C₁-C₆₀ alkyl group),and examples thereof include a methoxy group, an ethoxy group, and anisopropyloxy group.

The term “C₃-C₁₀ cycloalkyl group” as used herein refers to a monovalentsaturated hydrocarbon monocyclic group having 3 to 10 carbon atoms, andexamples thereof include a cyclopropyl group, a cyclobutyl group, acyclopentyl group, a cyclohexyl group, and a cycloheptyl group. The term“C₃-C₁₀ cycloalkylene group” as used herein refers to a divalent grouphaving substantially the same structure as the C₃-C₁₀ cycloalkyl group,except that the C₃-C₁₀ cycloalkylene group is divalent.

The term “C₁-C₁₀ heterocycloalkyl group” as used herein refers to amonovalent monocyclic group having at least one heteroatom selected fromN, O, Si, P, and S as a ring-forming atom and 1 to 10 carbon atoms, andexamples thereof include a 1,2,3,4-oxatriazolidinyl group, atetrahydrofuranyl group, and a tetrahydrothiophenyl group. The term“C₁-C₁₀ heterocycloalkylene group” as used herein refers to a divalentgroup having substantially the same structure as the C₁-C₁₀heterocycloalkyl group, except that the C₁-C₁₀ heterocycloalkylene groupis divalent.

The term “C₃-C₁₀ cycloalkenyl group” as used herein refers to amonovalent monocyclic group that has 3 to 10 carbon atoms and at leastone carbon-carbon double bond in the ring thereof and no aromaticity,and examples thereof include a cyclopentenyl group, a cyclohexenylgroup, and a cycloheptenyl group. The term “C₃-C₁₀ cycloalkenylenegroup” as used herein refers to a divalent group having substantiallythe same structure as the C₃-C₁₀ cycloalkenyl group, except that theC₃-C₁₀ cycloalkenylene group is divalent.

The term “C₁-C₁₀ heterocycloalkenyl group” as used herein refers to amonovalent monocyclic group that has at least one heteroatom selectedfrom N, O, Si, P, and S as a ring-forming atom, 1 to 10 carbon atoms,and at least one carbon-carbon double bond in its ring. Non-limitingexamples of the C₁-C₁₀ heterocycloalkenyl group include a4,5-dihydro-1,2,3,4-oxatriazolyl group, a 2,3-dihydrofuranyl group, anda 2,3-dihydrothiophenyl group. The term “C₁-C₁₀ heterocycloalkenylenegroup” as used herein refers to a divalent group having substantiallythe same structure as the C₁-C₁₀ heterocycloalkenyl group, except thatthe C₁-C₁₀ heterocycloalkenylene group is divalent.

The term “C₆-C₆₀ aryl group” as used herein refers to a monovalent grouphaving a carbocyclic aromatic system having 6 to 60 carbon atoms, and aC₆-C₆₀ arylene group used herein refers to a divalent group having acarbocyclic aromatic system having 6 to 60 carbon atoms. Non-limitingexamples of the C₆-C₆₀ aryl group include a phenyl group, a naphthylgroup, an anthracenyl group, a phenanthrenyl group, a pyrenyl group, anda chrysenyl group. When the C₆-C₆₀ aryl group and the C₆-C₆₀ arylenegroup each include two or more rings, the rings may be fused to eachother (e.g., combined together).

The term “C₁-C₆₀ heteroaryl group” as used herein refers to a monovalentgroup having a carbocyclic aromatic system that has at least oneheteroatom selected from N, O, Si, P, and S as a ring-forming atom, inaddition to 1 to 60 carbon atoms. The term “C₁-C₆₀ heteroarylene group”as used herein refers to a divalent group having a carbocyclic aromaticsystem that has at least one heteroatom selected from N, O, Si, P, and Sas a ring-forming atom, in addition to 1 to 60 carbon atoms.Non-limiting examples of the C₁-C₆₀ heteroaryl group include a pyridinylgroup, a pyrimidinyl group, a pyrazinyl group, a pyridazinyl group, atriazinyl group, a quinolinyl group, and an isoquinolinyl group. Whenthe C₁-C₆₀ heteroaryl group and the C₁-C₆₀ heteroarylene group eachinclude two or more rings, the rings may be condensed with each other(e.g., combined together).

The term “C₆-C₆₀ aryloxy group” as used herein refers to —OA₁₀₂ (whereinA₁₀₂ is the C₆-C₆₀ aryl group), and a C₆-C₆₀ arylthio group used hereinindicates —SA₁₀₃ (wherein A₁₀₃ is the C₆-C₆₀ aryl group).

The term “monovalent non-aromatic condensed polycyclic group” as usedherein refers to a monovalent group (for example, having 8 to 60 carbonatoms) having two or more rings condensed with each other (e.g.,combined together), only carbon atoms as ring-forming atoms, and noaromaticity in its entire molecular structure. A detailed example of themonovalent non-aromatic condensed polycyclic group includes a fluorenylgroup. The term “divalent non-aromatic condensed polycyclic group,” usedherein, refers to a divalent group having substantially the samestructure as the monovalent non-aromatic condensed polycyclic group,except that the divalent non-aromatic condensed polycyclic group isdivalent.

The term “monovalent non-aromatic condensed heteropolycyclic group” asused herein refers to a monovalent group (for example, having 1 to 60carbon atoms) having two or more rings condensed to each other, at leastone heteroatom selected from N, O, Si, P, and S, other than carbonatoms, as a ring-forming atom, and no aromaticity in its entiremolecular structure. An example of the monovalent non-aromatic condensedheteropolycyclic group includes a carbazolyl group. The term “divalentnon-aromatic condensed heteropolycyclic group” as used herein refers toa divalent group having substantially the same structure as themonovalent non-aromatic condensed heteropolycyclic group, except thatthe divalent non-aromatic condensed heteropolycyclic group is divalent.

The term “C₄-C₆₀ carbocyclic group” as used herein refers to amonocyclic or polycyclic group having 4 to 60 carbon atoms in which aring-forming atom is a carbon atom only. The C₄-C₆₀ carbocyclic groupmay be an aromatic carbocyclic group or a non-aromatic carbocyclicgroup. The C₄-C₆₀ carbocyclic group may be a ring, such as benzene, amonovalent group, such as a phenyl group, or a divalent group, such as aphenylene group. In one or more embodiments, depending on the number ofsubstituents connected to the C₄-C₆₀ carbocyclic group, the C₄-C₆₀carbocyclic group may be a trivalent group or a quadrivalent group.

The term “C₂-C₆₀ heterocyclic group” as used herein refers to a grouphaving the same structure as the C₄-C₆₀ carbocyclic group, except thatas a ring-forming atom, at least one heteroatom selected from N, O, Si,P, and S is used in addition to carbon (the number of carbon atoms maybe in a range of 2 to 60).

At least one substituent of the substituted C₄-C₆₀ carbocyclic group,the substituted C₂-C₆₀ heterocyclic group, the substituted C₃-C₁₀cycloalkylene group, the substituted C₁-C₁₀ heterocycloalkylene group,the substituted C₃-C₁₀ cycloalkenylene group, the substituted C₁-C₁₀heterocycloalkenylene group, the substituted C₆-C₆₀ arylene group, thesubstituted C₁-C₆₀ heteroarylene group, the substituted divalentnon-aromatic condensed polycyclic group, the substituted divalentnon-aromatic condensed heteropolycyclic group, the substituted C₁-C₆₀alkyl group, the substituted C₂-C₆₀ alkenyl group, the substitutedC₂-C₆₀ alkynyl group, the substituted C₁-C₆₀ alkoxy group, thesubstituted C₃-C₁₀ cycloalkyl group, the substituted C₁-C₁₀heterocycloalkyl group, the substituted C₃-C₁₀ cycloalkenyl group, thesubstituted C₁-C₁₀ heterocycloalkenyl group, the substituted C₆-C₆₀ arylgroup, the substituted C₆-C₆₀ aryloxy group, the substituted C₆-C₆₀arylthio group, the substituted C₁-C₆₀ heteroaryl group, the substitutedmonovalent non-aromatic condensed polycyclic group, and the substitutedmonovalent non-aromatic condensed heteropolycyclic group may be selectedfrom:

deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, a nitrogroup, an amidino group, a hydrazino group, a hydrazono group, a C₁-C₆₀alkyl group, a C₂-C₆₀ alkenyl group, a C₂-C₆₀ alkynyl group, and aC₁-C₆₀ alkoxy group;

a C₁-C₆₀ alkyl group, a C₂-C₆₀ alkenyl group, a C₂-C₆₀ alkynyl group,and a C₁-C₆₀ alkoxy group, each substituted with at least one selectedfrom deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, anitro group, an amidino group, a hydrazino group, a hydrazono group, aC₃-C₁₀ cycloalkyl group, a C₁-C₁₀ heterocycloalkyl group, a C₃-C₁₀cycloalkenyl group, a C₁-C₁₀ heterocycloalkenyl group, a C₆-C₆₀ arylgroup, a C₆-C₆₀ aryloxy group, a C₆-C₆₀ arylthio group, a C₁-C₆₀heteroaryl group, a monovalent non-aromatic condensed polycyclic group,a monovalent non-aromatic condensed heteropolycyclic group,—Si(Q₁₁)(Q₁₂)(Q₁₃), —N(Q₁₁)(Q₁₂), —B(Q₁₁)(Q₁₂), —C(═O)(Q₁₁),—S(═O)₂(Q₁₁), and —P(═O)(Q₁₁)(Q₁₂);

a C₃-C₁₀ cycloalkyl group, a C₁-C₁₀ heterocycloalkyl group, a C₃-C₁₀cycloalkenyl group, a C₁-C₁₀ heterocycloalkenyl group, a C₆-C₆₀ arylgroup, a C₆-C₆₀ aryloxy group, a C₆-C₆₀ arylthio group, a C₁-C₆₀heteroaryl group, a monovalent non-aromatic condensed polycyclic group,and a monovalent non-aromatic condensed heteropolycyclic group;

a C₃-C₁₀ cycloalkyl group, a C₁-C₁₀ heterocycloalkyl group, a C₃-C₁₀cycloalkenyl group, a C₁-C₁₀ heterocycloalkenyl group, a C₆-C₆₀ arylgroup, a C₆-C₆₀ aryloxy group, a C₆-C₆₀ arylthio group, a C₁-C₆₀heteroaryl group, a monovalent non-aromatic condensed polycyclic group,and a monovalent non-aromatic condensed heteropolycyclic group, eachsubstituted with at least one selected from deuterium, —F, —Cl, —Br, —I,a hydroxyl group, a cyano group, a nitro group, an amidino group, ahydrazino group, a hydrazono group, a C₁-C₆₀ alkyl group, a C₂-C₆₀alkenyl group, a C₂-C₆₀ alkynyl group, a C₁-C₆₀ alkoxy group, a C₃-C₁₀cycloalkyl group, a C₁-C₁₀ heterocycloalkyl group, a C₃-C₁₀ cycloalkenylgroup, a C₁-C₁₀ heterocycloalkenyl group, a C₆-C₆₀ aryl group, a C₆-C₆₀aryloxy group, a C₆-C₆₀ arylthio group, a C₁-C₆₀ heteroaryl group, amonovalent non-aromatic condensed polycyclic group, a monovalentnon-aromatic condensed heteropolycyclic group, —Si(Q₂₁)(Q₂₂)(Q₂₃),—N(Q₂₁)(Q₂₂), —B(Q₂₁)(Q₂₂), —C(═O)(Q₂₁), —S(═O)₂(Q₂₁), and—P(═O)(Q₂₁)(Q₂₂); and

—Si(Q₃₁)(Q₃₂)(Q₃₃), —N(Q₃₁)(Q₃₂), —B(Q₃₁)(Q₃₂), —C(═O)(Q₃₁),—S(═O)₂(Q₃₁), and —P(═O)(Q₃₁)(Q₃₂), and

Q₁₁ to Q₁₃, Q₂₁ to Q₂₃, and Q₃₁ to Q₃₃ may each independently beselected from hydrogen, deuterium, —F, —Cl, —Br, —I, a hydroxyl group, acyano group, a nitro group, an amidino group, a hydrazino group, ahydrazono group, a C₁-C₆₀ alkyl group, a C₂-C₆₀ alkenyl group, a C₂-C₆₀alkynyl group, a C₁-C₆₀ alkoxy group, a C₃-C₁₀ cycloalkyl group, aC₁-C₁₀ heterocycloalkyl group, a C₃-C₁₀ cycloalkenyl group, a C₁-C₁₀heterocycloalkenyl group, a C₆-C₆₀ aryl group, a C₁-C₆₀ heteroarylgroup, a monovalent non-aromatic condensed polycyclic group, amonovalent non-aromatic condensed heteropolycyclic group, a C₁-C₆₀ alkylgroup substituted with at least one selected from deuterium, —F, and acyano group, a C₆-C₆₀ aryl group substituted with at least one selectedfrom deuterium, —F, and a cyano group, a biphenyl group, and a terphenylgroup.

The term “Ph” as used herein represents a phenyl group, the term “Me” asused herein represents a methyl group, the term “Et” as used hereinrepresents an ethyl group, the term “ter-Bu” or “Bu^(t),” as usedherein, represents a tert-butyl group, and the term “OMe” as used hereinrepresents a methoxy group.

The term “biphenyl group” used herein refers to “a phenyl group”substituted with a phenyl group. The “biphenyl group” may be “asubstituted phenyl group” having “a C₆-C₆₀ aryl group” as a substituent.

The term “terphenyl group” used herein refers to a “phenyl groupsubstituted with a biphenyl group. The “terphenyl group” may be “asubstituted phenyl group” including “a substituted C₆-C₆₀ aryl group”having “a C₆-C₆₀ aryl group” as a substituent.

*and *′ used herein, unless defined otherwise, each refer to a bindingsite to a neighboring atom in a corresponding formula.

Hereinafter, a compound according to embodiments and an organiclight-emitting device according to embodiments will be described in moredetail with reference to Synthesis Examples and Examples. The expression“B was used instead of A” used in describing Synthesis Examples meansthat an identical number of molar equivalents of A was used in place ofmolar equivalents of B.

EXAMPLES Synthesis Example 1: Synthesis of Compound 2

a) Synthesis of Intermediate A

5.26 g (16.7 mmol) of 1,3,5-tribromobenzene, 2.16 g (17.6 mmol) of2-pyridineboronic acid, 0.68 g (0.59 mmol) of Pd(PPh₃)₄, and 4.85 g(35.1 mmol) of K₂CO₃ were dissolved in 60 mL of tetrahydrofuran (THF)and 30 mL of distilled water and then stirred at a temperature of 80° C.for 12 hours. The reaction solution was cooled to room temperature, andan organic layer was extracted therefrom three times by using 50 mL ofwater and 50 mL of ethyl acetate. The obtained organic layer was driedby using magnesium sulfate, and a solvent was evaporated therefrom.Then, the residue obtained therefrom was separated and purified bysilica gel column chromatography to obtain 3.50 g of Intermediate A.

b) Synthesis of Intermediate B

3.50 g (11.3 mmol) of Intermediate A, 2.44 g (11.3 mmol) of3,5-dimethyl-1-phenyl-1H-pyrazole-4-yl)boronic acid, 0.46 g (0.40 mmol)of Pd(PPh₃)₄, and 3.28 g (23.8 mmol) of K₂CO₃ were dissolved in 50 mL ofTHF and 25 mL of distilled water and then stirred at a temperature of80° C. for 12 hours. The reaction solution was cooled to roomtemperature, and an organic layer was extracted therefrom three times byusing 50 mL of water and 50 mL of ethyl acetate. The obtained organiclayer was dried by using magnesium sulfate, and a solvent was evaporatedtherefrom. Then, the residue obtained therefrom was separated andpurified by silica gel column chromatography to obtain 3.38 g ofIntermediate B.

c) Synthesis of Compound 2

1.00 g (2.48 mmol) of Intermediate B and 1.03 g (2.48 mmol) of K₂PtCl₄were suspended in 120 mL of acetic acid and then stirred at atemperature of 110° C. for 3 days. The reaction solution was cooled toroom temperature, and a precipitate was filtered therefrom, sequentiallywashed by using methanol, distilled water, ethanol, and diethylether,and then dried. A solid obtained therefrom was separated and purified bycolumn chromatography to obtain 0.80 g of Compound 2.

Synthesis Example 2: Synthesis of Compound 3

0.65 g of Compound 3 was synthesized in substantially the same manner asin Synthesis Example 1, except that2,2′-(5-(1,3,5-triphenyl-1H-pyrazol-4-yl)-1,3-phenylene)dipyridine wasused instead of Intermediate B.

Synthesis Example 3: Synthesis of Compound 28

a) Synthesis of Intermediate A

2.40 g (12.05 mmol) of 2-methoxycarbazole, 4.28 g (18.05 mmol) of3,5-dibromopyridine, 1.53 g (24.10 mmol) of Cu powder, 6.65 g (48.20mmol) of potassium carbonate, and 0.315 g (1.200 mmol) of 18-Crown-6were suspended in 50 mL of dimethylformamide purified by fractionaldistillation, and then stirred at a temperature of 150° C. for 10 hours.An organic layer was extracted from the reaction mixture by using ethylacetate and distilled water. The extracted organic layer was dried byusing magnesium sulfate and then filtered. Then, the residue obtainedtherefrom was purified by column chromatography(1/3=dichloromethane/normal hexane) to obtain 1.6 g of Intermediate A.

b) Synthesis of Intermediate B

1.6 g (4.50 mmol) of Intermediate A, 1.46 g (6.75 mmol) of(3,5-dimethyl-1-phenyl-1H-pyrazol-4-yl)boronic acid, 1.24 g (9.00 mmol)of potassium carbonate, and 0.30 g (0.27 mmol) of Pd(PPh₃)₄ weresuspended in 150 mL of a mixed solvent in which a ratio of toluene todistilled water was 4/1, and then stirred at a temperature of 80° C. for18 hours. An organic layer was extracted from the reaction mixture byusing dichloromethane and distilled water. The extracted organic layerwas dried by using magnesium sulfate and then filtered. Then, theresidue obtained therefrom was purified by column chromatography(1/30=methanol/dichloromethane) to obtain 1.7 g of Intermediate B.

c) Synthesis of Intermediate C

1.7 g (3.82 mmol) of Intermediate B was dissolved in 150 mL ofdichloromethane and cooled to a temperature of −78° C. 7.83 mL (7.83mmol) of BBr₃ (1.0 M in n-hexane) was added thereto, stirred for 1 hour,heated to a temperature of 0° C., and then stirred for 2 hours. Thereaction was terminated by a sodium bicarbonate aqueous solution, and anorganic layer was extracted therefrom by using dichloromethane. Theextracted organic layer was dried by magnesium sulfate and thenfiltered. Then, the residue obtained therefrom was purified by columnchromatography (1/2=ethyl acetate/normal hexane) to obtain 1.3 g ofIntermediate C.

d) Synthesis of Intermediate D

1.2 g (2.79 mmol) of Intermediate C, 1.0 g (3.20 mmol) of2-bromo-9-(pyridin-2-yl)-carbazole, 0.14 g (1.06 mmol) of picolinicacid, 0.11 g (0.53 mmol) of copper(I) iodide, and 1.14 g (5.58 mmol) ofpotassium phosphate were added to a round-bottom flask and suspended in100 mL of dimethylsulfoxide. The reaction mixture was heated to atemperature of 120° C. and stirred for 20 hours. An organic layer wasextracted from the reaction mixture by using ethyl acetate and distilledwater. The extracted organic layer was dried by using magnesium sulfateand then filtered. Then, the residue obtained therefrom was purified bycolumn chromatography (1/1=ethyl acetate/normal hexane) to obtain 1.0 gof Intermediate D.

e) Synthesis of Compound 28

0.35 g (0.52 mmol) of Intermediate D, 0.23 g (0.54 mmol) of potassiumtetrachloroplatinate, and 0.017 g (0.052 mmol) of Bu₄NBr were suspendedin 30 mL of acetic acid. The reaction solution was bubbled with nitrogenfor 30 minutes and stirred at room temperature for 8 hours. The reactionmixture was heated to a temperature of 120° C. and additionally stirredfor 36 hours. Then, the reaction mixture was cooled to room temperature,and 100 mL of distilled water was added thereto. A precipitate wasfiltered therefrom, washed three times by using distilled water, andthen dried with warm air. Then, a solid obtained therefrom was purifiedby column chromatography (1/1=dichloromethane/normal hexane) to obtain0.24 g of Compound 28.

Synthesis Example 4: Synthesis of Compound 17

0.85 g of Compound 17 was synthesized in substantially the same manneras in Synthesis Example 3, except that2-(3-(3,5-dimethyl-1-phenyl-1H-pyrazol-4-yl)-5-(1-methyl-1H-imidazol-2-yl)phenoxy)-9-(pyridin-2-yl)-9H-carbazolewas used instead of Intermediate D.

Synthesis Example 5: Synthesis of Compound 22

1.00 g of Compound 22 was synthesized in substantially the same manneras in Synthesis Example 3, except that2-(3-(3-(3,5-dimethyl-1-phenyl-1H-pyrazol-4-yl)-5-(1-methyl-1H-314-imidazol-3-yl)phenoxy)phenoxy)pyridinewas used instead of Intermediate D.

Synthesis Example 6: Synthesis of Compound 24

1.28 g of Compound 24 was synthesized in substantially the same manneras in Synthesis Example 3, except thatN-(3-(3,5-dimethyl-1-phenyl-1H-pyrazol-4-yl)-5-((9-(pyridin-2-yl)-9H-carbazol-2-yl)oxy)phenyl)-N-phenylpyridin-2-aminewas used instead of Intermediate D.

Synthesis Example 7: Synthesis of Compound 26

0.55 g of Compound 26 was synthesized in substantially the same manneras in Synthesis Example 3, except that2-(3-(3,5-dimethyl-1-phenyl-1H-pyrazol-4-yl)-5-(1-methyl-1H-imidazol-2-yl)phenoxy)-9-(1-methyl-1H-imidazol-2-yl)-9H-carbazolewas used instead of Intermediate D.

Synthesis Example 8: Synthesis of Compound 2

1.05 g of Compound 40 was synthesized in substantially the same manneras in Synthesis Example 3, except that9-(4-(3,5-dimethyl-1-phenyl-1H-pyrazol-4-yl)pyridin-2-yl)-2-((9-(4-methylpyridin-2-yl)-9H-carbazol-2-yl)oxy)-9H-carbazolewas used instead of Intermediate D.

Synthesis Example 9: Synthesis of Compound 41

0.88 g of Compound 41 was synthesized in substantially the same manneras in Synthesis Example 3, except that((9-(4-phenylpyridin-2-yl)-9H-carbazol-2-yl)oxy)-9H-carbazole was usedinstead of Intermediate D.

Synthesis Example 10: Synthesis of Compound 42

0.85 g of Compound 42 was synthesized in substantially the same manneras in Synthesis Example 3, except that9-(4-(3,5-dimethyl-1-phenyl-1H-pyrazol-4-yl)pyridin-2-yl)-2-((9-(4-isopropylpyridin-2-yl)-9H-carbazol-2-yl)oxy)-9H-carbazolewas used instead of Intermediate D.

High resolution electron impact mass spectrometry (HR-EIMS) values and¹H nuclear magnetic resonance (NMR) measurement results measured for theSynthesis Examples are shown in Table 1 below.

TABLE 1 HR-EIMS Compound ¹H NMR (CDCl₃, 500 MHz) found calc. 2δ8.42~8.44 (m, 2H), 8.13~8.16(m, 2H), 7.99~8.12(m, 2H), 632.0329632.0355 7.62~7.65(m, 2H), 7.37~7.47(m, 3H), 7.10~7.13(m, 4H), 2.20(s,3H), 2.14(s, 3H) 3 δ8.45~8.47(m, 2H), 7.99~8.13(m, 4H), 7.66~7.69(m,2H), 756.1723 756.1754 7.45~7.51 (m, 6H), 7.35~7.38(m, 4H), 7.28~7.33(m,3H), 7.17 (d, 2H), 7.12(d, 2H) 17 δ7.98~8.10(m, 2H), 7.85(d, 1H),7.80(d, 1H), 7.61~7.64 (m, 779.7715 779.7756 3H), 7.47~7.49(m, 2H),7.37(d, 2H), 7.25~7.29 (m, 3H), 7.24(m, 1H), 7.09(d, 2H), 6.84(d, 1H),6.77(d, 1H), 6.44(m, 1H), 6.22(m, 1H), 3.57(s, 3H), 2.20(s, 3H), 2.14(s,3H) 22 δ8.08~8.12(d, 2H), 7.63(d, 2H), 7.37~7.40(m, 3H), 7.06(d,829.8341 829.8382 2H), 6.93(d, 2H), 6.45~6.55(m, 4H), 6.11~6.20(m, 4H),5.70(m, 1H), 3.10(s, 3H), 2.23(s, 3H), 2.15(s, 3H) 24 δ8.31 (d, 1H),8.06~8.09(m, 2H), 7.85~7.88(m, 2H), 7.59~7.63(m, 867.8818 867.8847 3H),7.37~7.42(m, 5H), 7.30~7.33(m, 2H), 7.10~7.18(m, 3H), 6.78~6.84(m, 3H),6.55~6.57(m, 2H), 6.47(d, 2H), 6.06(d, 1H), 2.20(s, 3H), 2.13(s, 3H) 26δ8.25~8.27(d, 1H), 8.05~8.10(m, 2H), 7.93(m, 2H), 7.88(m, 2H), 782.7754782.7720 7.62~7.66(m, 3H), 7.32~7.39(m, 7H), 7.08~7.13(m, 2H),6.74~6.80(m, 3H), 6.55~6.57(m, 2H), 6.47(d, 2H), 6.06(d, 1H), 2.21(s,3H), 2.15(s, 3H) 28 δ7.94~8.10(m, 7H), 7.83~7.85(m, 2H), 7.68(d, 1H),7.59~7.64(m, 865.8634 865.8683 4H), 7.48(m, 1H), 7.37(d, 2H), 7.29(m,2H), 7.02~7.08(m, 3H), 6.58~7.03(m, 2H), 2.33(s, 3H), 2.30(s, 3H) 40δ7.99~8.08(m, 5H), 7.79~7.84(m, 3H), 7.64~7.68(m, 3H), 7.60(d, 879.8921879.8944 2H), 7.35~7.38(m, 3H), 7.29(m, 2H), 7.12(d, 1H), 7.00~7.03(m,2H), 6.59(m, 2H), 2.29(s, 3H), 2.25(s, 3H), 2.20(s, 3H) 41 δ8.02~8.10(m,5H), 7.73~7.82(m, 6H), 7.60~7.63(m, 4H), 7.57(m, 941.9682 941.9637 2H),7.39~7.45(m, 6H), 7.29(m, 2H), 6.58~7.03(m, 3H), 2.28(s, 3H), 2.24(s,3H) 42 δ7.99~8.09(m, 6H), 7.77~7.81(m, 3H), 7.61~7.65(m, 4H), 907.9453907.9415 7.46~7.48(m, 2H), 7.37(d, 2H), 7.29(m, 2H), 6.94(m, 1H),6.66~7.68(m, 1H), 6.59(d, 2H), 2.97(m, 1H), 2.29(s, 3H), 2.26(s, 3H),1.45(s, 6H)

Example 1

As a substrate and an ITO anode, a Corning 15 Ω/cm² (1,200 Å) ITO glasssubstrate was cut to a size of 50 mm×50 mm×0.7 mm, sonicated withisopropyl alcohol and pure water each for 5 minutes, and then cleaned byexposure to ultraviolet rays and ozone for 30 minutes. Then, theresultant ITO glass substrate was provided to a vacuum depositionapparatus.

2-TNATA was vacuum-deposited on the ITO anode formed on the ITO glasssubstrate to form a hole injection layer having a thickness of 600 Å,and NPB was vacuum-deposited on the hole injection layer to form a holetransport layer having a thickness of 300 Å.

BCPDS (bis(4-(9H-carbazol-9-yl)phenyl)diphenylsilane) and POPCPA((4-{1-[4-(diphenylphosphoryl)phenyl]cyclohexyl}phenyl)diphenylamine)(co-host) (weight ratio of BCPDS to POPCPA was 1:1), and Compound 1(dopant), were co-deposited on the hole transport layer at a weightratio of the co-host to the dopant of 90:10, thereby forming an emissionlayer having a thickness of 300 Å.

TSPO1 (diphenyl-4-triphenylsilyl-phenylphosphine oxide) was deposited onthe emission layer to form a hole blocking layer having a thickness of50 Å, Alq₃ was deposited on the hole blocking layer to form an electrontransport layer having a thickness of 300 Å, LiF was deposited on theelectron transport layer to form an electron injection layer having athickness of 10 Å, and Al was vacuum-deposited on the electron injectionlayer to form a cathode having a thickness of 3,000 Å, therebycompleting the manufacture of an organic light-emitting device.

Examples 2 to 10 and Comparative Examples 1 to 4

Organic light-emitting devices were manufactured in substantially thesame manner as in Example 1, except that Compounds shown in Table 2 wereeach used instead of Compound 1 as a dopant in forming an emissionlayer.

Evaluation Example 1

The driving voltage, current density, luminance, luminescent efficiency,and maximum emission wavelength of the organic light-emitting devicesmanufactured according to Examples 1 to 10 and Comparative Examples 1 to4 were measured by using Keithley SMU 236 and a luminance meter PR650,and evaluation results thereof are shown in Table 2.

TABLE 2 Maximum Driving Current Luminescent emission voltage densityLuminance efficiency Emission wavelength Dopant (V) (mA/cm²) (cd/m²)(cd/A) color (nm) Example 1 Compound 2 3.4 0.09 15 17.8 Blue 450 Example2 Compound 3 3.4 0.08 15 18.2 Blue 449 Example 3 Compound 17 3.3 0.08 1518.1 Blue 452 Example 4 Compound 18 3.3 0.08 15 18.2 Blue 446 Example 5Compound 24 3.3 0.09 15 17.6 Blue 450 Example 6 Compound 26 3.3 0.08 1518.1 Blue 451 Example 7 Compound 28 3.4 0.08 15 18.2 Blue 455 Example 8Compound 40 3.4 0.06 15 18.6 Blue 456 Example 9 Compound 41 3.3 0.10 1516.4 Blue 448 Example 10 Compound 42 3.4 0.10 15 16.9 Blue 448Comparative Comparative 3.9 0.09 15 10.2 Green 514 Example 1 Compound AComparative Comparative 4.5 0.11 15 13.8 Blue 455 Example 2 Compound BComparative Comparative 3.7 0.15 15 15.5 Light blue 490 Example 3Compound C Comparative Comparative 5.2 0.09 15 17.0 Blue 473 Example 4Compound D

Referring to Table 2, it is confirmed that the organic light-emittingdevices of Examples 1 to 10 have a low driving voltage, high luminance,and high luminescent efficiency, and are suitable for deep blue lightemission, as compared with those of the organic light-emitting devicesof Comparative Examples 1 to 4.

According to one or more embodiments, an organic light-emitting deviceincluding the organometallic compound may have a low driving voltage,high luminescent efficiency, high luminance, and a long lifespan.

It should be understood that embodiments described herein should beconsidered in a descriptive sense only and not for purposes oflimitation. Descriptions of features or aspects within each embodimentshould typically be considered as available for other similar featuresor aspects in other embodiments.

As used herein, the terms “combination thereof” and “combinationsthereof” may refer to a chemical combination (e.g., an alloy or chemicalcompound), a mixture, or a laminated structure of components.

It will be understood that, although the terms “first,” “second,”“third,” etc., may be used herein to describe various elements,components, regions, layers and/or sections, these elements, components,regions, layers and/or sections should not be limited by these terms.These terms are used to distinguish one element, component, region,layer or section from another element, component, region, layer orsection. Thus, a first element, component, region, layer or sectiondescribed below could be termed a second element, component, region,layer or section, without departing from the spirit and scope of thepresent disclosure.

Spatially relative terms, such as “beneath,” “below,” “lower,” “under,”“above,” “upper,” and the like, may be used herein for ease ofexplanation to describe one element or feature's relationship to anotherelement(s) or feature(s) as illustrated in the figures. It will beunderstood that the spatially relative terms are intended to encompassdifferent orientations of the device in use or in operation, in additionto the orientation depicted in the figures. For example, if the devicein the figures is turned over, elements described as “below” or“beneath” or “under” other elements or features would then be oriented“above” the other elements or features. Thus, the example terms “below”and “under” can encompass both an orientation of above and below. Thedevice may be otherwise oriented (e.g., rotated 90 degrees or at otherorientations) and the spatially relative descriptors used herein shouldbe interpreted accordingly.

It will be understood that when an element or layer is referred to asbeing “on,” “connected to,” or “coupled to” another element or layer, itcan be directly on, connected to, or coupled to the other element orlayer, or one or more intervening elements or layers may be present. Inaddition, it will also be understood that when an element or layer isreferred to as being “between” two elements or layers, it can be theonly element or layer between the two elements or layers, or one or moreintervening elements or layers may also be present.

The terminology used herein is for the purpose of describing particularembodiments only and is not intended to be limiting of the presentdisclosure. As used herein, the singular forms “a” and “an” are intendedto include the plural forms as well, unless the context clearlyindicates otherwise. It will be further understood that the terms“comprises,” “comprising,” “includes,” and “including,” when used inthis specification, specify the presence of the stated features,integers, acts, operations, elements, and/or components, but do notpreclude the presence or addition of one or more other features,integers, acts, operations, elements, components, and/or groups thereof.

As used herein, the terms “substantially,” “about,” and similar termsare used as terms of approximation and not as terms of degree, and areintended to account for the inherent deviations in measured orcalculated values that would be recognized by those of ordinary skill inthe art. Further, the use of “may” when describing embodiments of thepresent disclosure refers to “one or more embodiments of the presentdisclosure.” As used herein, the terms “use,” “using,” and “used” may beconsidered synonymous with the terms “utilize,” “utilizing,” and“utilized,” respectively. Also, the term “exemplary” is intended torefer to an example or illustration.

Also, any numerical range recited herein is intended to include allsub-ranges of the same numerical precision subsumed within the recitedrange. For example, a range of “1.0 to 10.0” is intended to include allsubranges between (and including) the recited minimum value of 1.0 andthe recited maximum value of 10.0, that is, having a minimum value equalto or greater than 1.0 and a maximum value equal to or less than 10.0,such as, for example, 2.4 to 7.6. Any maximum numerical limitationrecited herein is intended to include all lower numerical limitationssubsumed therein, and any minimum numerical limitation recited in thisspecification is intended to include all higher numerical limitationssubsumed therein. Accordingly, Applicant reserves the right to amendthis specification, including the claims, to expressly recite anysub-range subsumed within the ranges expressly recited herein.

While one or more embodiments have been described with reference to theaccompanying drawing, it will be understood by those of ordinary skillin the art that various changes in form and details may be made thereinwithout departing from the spirit and scope as defined by the followingclaims, and equivalents thereof.

What is claimed is:
 1. An organometallic compound represented by Formula1:

wherein M in Formula 1 is Pt, Pd, Ir, or Os, in Formula 1, L₁ is aligand represented by Formula 2A or 2B, and n1 is 1 or 2, wherein, whenn1 is two, two L₁(s) are identical to or different from each other, inFormula 1, L₂ is a monovalent organic ligand or a divalent organicligand, and n2 is 0, 1, or 2, the sum of n1 and n2 in Formula 1 is 1, 2,or 3, ^(*1), ^(*2) and ^(*3) in Formula 2A and ^(*1), ^(*2), ^(*3), and^(*4) in Formula 2B each indicate a binding site to M in Formula 1, X₁is N or C, X₂ is N or C, X₃ is N or C, and X₄ is N or C, Y₁ to Y₈ areeach independently N or C, a bond between X₁ and Y₁ is a single bond ora double bond, a bond between X₁ and Y₂ is a single bond or a doublebond, a bond between X₂ and Y₃ is a single bond or a double bond, a bondbetween X₂ and Y₄ is a single bond or a double bond, a bond between X₃and Y₅ is a single bond or a double bond, a bond between X₃ and Y₆ is asingle bond or a double bond, rings A₁ to A₄ are each independently aC₅-C₃₀ carbocyclic group or a C₂-C₆₀ heterocyclic group, T₁ to T₃ areeach independently selected from *—N[(L₅)_(a5)-(R₁₅)]—*, *—B(R₁₅)—*,*—P(R₁₅)—*′, *—C(R₁₅)(R₁₅)—*′, *—Si(R₁₅)(R₁₅)—*′, *—Ge(R₁₅)(R₁₆)—*′,*—S—*′, *—Se—*′, *—O—*, *—C(═O)—*′, *—S(═O)—*′, *—S(═O)₂—*′,*—C(R₁₅)=*′, *═C(R₁₅)—*′, *—C(R₁₅)═C(R₁₆)—*′, *—C(═S)—*′, and *—C≡C—*′,a5 is selected from 1 to 3, wherein, when a5 is two or more, two or moreL₅(s) are identical to or different from each other, R₁₅ and R₁₆ areoptionally linked to a neighboring substituent selected from R₁₁ to R₁₄to form a substituted or unsubstituted C₅-C₃₀ carbocyclic group or asubstituted or unsubstituted C₁-C₃₀ heterocyclic group, b1 to b4 areeach independently 0, 1, 2, or 3, wherein, when b1 is zero,*-(T₁)_(b1)-*′ is a single bond, when b2 is zero, *-(T₂)_(b2)-*′ is asingle bond, when b3 is zero, *(T₃)_(b3)-*′ is a single bond, and whenb4 is zero, *-(T₄)_(b4)-*′ is a single bond, *and*′ each indicate abinding site to a neighboring atom, Z₁ to Z₄ are each represented byFormula 3, c1 to c4 are each independently 0, 1, 2, or 3, the sum of c1,c2, and c3 in Formula 2A is one or more, the sum of c1, c2, c3, and c4in Formula 2B is one or more, T₅ in Formula 3 is a substituted orunsubstituted C₅-C₃₀ carbocyclic group or a substituted or unsubstitutedC₂-C₆₀ heterocyclic group, b5 is an integer from 0 to 5, X₅ is O, S, orN(R₃), R₁ to R₃ and R₁₁ to R₁₆ are each independently selected fromhydrogen, deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group,a nitro group, an amidino group, a hydrazino group, a hydrazono group, asubstituted or unsubstituted C₁-C₆₀ alkyl group, a substituted orunsubstituted C₂-C₆₀ alkenyl group, a substituted or unsubstitutedC₂-C₆₀ alkynyl group, a substituted or unsubstituted C₁-C₆₀ alkoxygroup, a substituted or unsubstituted C₃-C₁₀ cycloalkyl group, asubstituted or unsubstituted C₁-C₁₀ heterocycloalkyl group, asubstituted or unsubstituted C₃-C₁₀ cycloalkenyl group, a substituted orunsubstituted C₁-C₁₀ heterocycloalkenyl group, a substituted orunsubstituted C₆-C₆₀ aryl group, a substituted or unsubstituted C₆-C₆₀aryloxy group, a substituted or unsubstituted C₆-C₆₀ arylthio group, asubstituted or unsubstituted C₁-C₆₀ heteroaryl group, a substituted orunsubstituted monovalent non-aromatic condensed polycyclic group, asubstituted or unsubstituted monovalent non-aromatic condensedheteropolycyclic group, —Si(Q₁)(Q₂)(Q₃), —N(Q₁)(Q₂), —B(Q₁)(Q₂),—C(═O)(Q₁), —S(═O)₂(Q₁), and —P(═O)(Q₁)(Q₂), at least one substituent ofthe substituted C₁-C₆₀ alkyl group, the substituted C₂-C₆₀ alkenylgroup, the substituted C₂-C₆₀ alkynyl group, the substituted C₁-C₆₀alkoxy group, the substituted C₃-C₁₀ cycloalkyl group, the substitutedC₁-C₁₀ heterocycloalkyl group, the substituted C₃-C₁₀ cycloalkenylgroup, the substituted C₁-C₁₀ heterocycloalkenyl group, the substitutedC₆-C₆₀ aryl group, the substituted C₆-C₆₀ aryloxy group, the substitutedC₆-C₆₀ arylthio group, the substituted C₁-C₆₀ heteroaryl group, thesubstituted monovalent non-aromatic condensed polycyclic group, thesubstituted monovalent non-aromatic condensed heteropolycyclic group,the substituted C₄-C₆₀ carbocyclic group, and the substituted C₂-C₆₀heterocyclic group is selected from: deuterium, —F, —Cl, —Br, —I, ahydroxyl group, a cyano group, a nitro group, an amidino group, ahydrazino group, a hydrazono group, a C₁-C₆₀ alkyl group, a C₂-C₆₀alkenyl group, a C₂-C₆₀ alkynyl group, and a C₁-C₆₀ alkoxy group; aC₁-C₆₀ alkyl group, a C₂-C₆₀ alkenyl group, a C₂-C₆₀ alkynyl group, anda C₁-C₆₀ alkoxy group, each substituted with at least one selected fromdeuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, a nitrogroup, an amidino group, a hydrazino group, a hydrazono group, a C₃-C₁₀cycloalkyl group, a C₁-C₁₀ heterocycloalkyl group, a C₃-C₁₀ cycloalkenylgroup, a C₁-C₁₀ heterocycloalkenyl group, a C₆-C₆₀ aryl group, a C₆-C₆₀aryloxy group, a C₆-C₆₀ arylthio group, a C₁-C₆₀ heteroaryl group, amonovalent non-aromatic condensed polycyclic group, a monovalentnon-aromatic condensed heteropolycyclic group, —Si(Q₁₁)(Q₁₂)(Q₁₃),—N(Q₁₁)(Q₁₂), —B(Q₁₁)(Q₁₂), —C(═O)(Q₁₁), —S(═O)₂(Q₁₁), and—P(═O)(Q₁₁)(Q₁₂); a C₃-C₁₀ cycloalkyl group, a C₁-C₁₀ heterocycloalkylgroup, a C₃-C₁₀ cycloalkenyl group, a C₁-C₁₀ heterocycloalkenyl group, aC₆-C₆₀ aryl group, a C₆-C₆₀ aryloxy group, a C₆-C₆₀ arylthio group, aC₁-C₆₀ heteroaryl group, a monovalent non-aromatic condensed polycyclicgroup, and a monovalent non-aromatic condensed heteropolycyclic group; aC₃-C₁₀ cycloalkyl group, a C₁-C₁₀ heterocycloalkyl group, a C₃-C₁₀cycloalkenyl group, a C₁-C₁₀ heterocycloalkenyl group, a C₆-C₆₀ arylgroup, a C₆-C₆₀ aryloxy group, a C₆-C₆₀ arylthio group, a C₁-C₆₀heteroaryl group, a monovalent non-aromatic condensed polycyclic group,and a monovalent non-aromatic condensed heteropolycyclic group, eachsubstituted with at least one selected from deuterium, —F, —Cl, —Br, —I,a hydroxyl group, a cyano group, a nitro group, an amidino group, ahydrazino group, a hydrazono group, a C₁-C₆₀ alkyl group, a C₂-C₆₀alkenyl group, a C₂-C₆₀ alkynyl group, a C₁-C₆₀ alkoxy group, a C₃-C₁₀cycloalkyl group, a C₁-C₁₀ heterocycloalkyl group, a C₃-C₁₀ cycloalkenylgroup, a C₁-C₁₀ heterocycloalkenyl group, a C₆-C₆₀ aryl group, a C₆-C₆₀aryloxy group, a C₆-C₆₀ arylthio group, a C₁-C₆₀ heteroaryl group, amonovalent non-aromatic condensed polycyclic group, a monovalentnon-aromatic condensed heteropolycyclic group, —Si(Q₂₁)(Q₂₂)(Q₂₃),—N(Q₂₁)(Q₂₂), —B(Q₂₁)(Q₂₂), —C(═O)(Q₂₁), —S(═O)₂(Q₂₁), and—P(═O)(Q₂₁)(Q₂₂); and —Si(Q₃₁)(Q₃₂)(Q₃₃), —N(Q₃₁)(Q₃₂), —B(Q₃₁)(Q₃₂),—C(═O)(Q₃₁), —S(═O)₂(Q₃₁), and —P(═O)(Q₃₁)(Q₃₂), and Q₁ to Q₃, Q₁₁ toQ₁₃, Q₂₁ to Q₂₃, and Q₃₁ to Q₃₃ are each independently selected fromhydrogen, deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group,a nitro group, an amidino group, a hydrazino group, a hydrazono group, aC₁-C₆₀ alkyl group, a C₂-C₆₀ alkenyl group, a C₂-C₆₀ alkynyl group, aC₁-C₆₀ alkoxy group, a C₃-C₁₀ cycloalkyl group, a C₁-C₁₀heterocycloalkyl group, a C₃-C₁₀ cycloalkenyl group, a C₁-C₁₀heterocycloalkenyl group, a C₆-C₆₀ aryl group, a C₁-C₆₀ heteroarylgroup, a monovalent non-aromatic condensed polycyclic group, amonovalent non-aromatic condensed heteropolycyclic group, a biphenylgroup, and a terphenyl group.
 2. The organometallic compound of claim 1,wherein: M in Formula 1 is platinum, and n2 is
 0. 3. The organometalliccompound of claim 1, wherein: rings A₁ to A₄ are each independentlyselected from a benzene group, a naphthalene group, an anthracene group,a phenanthrene group, a fluorene group, a phenalene group, a pyrenegroup, a fluoranthene group, a tetracene group, a chrysene group, atriphenylene group, a benzofluorene group, a perylene group, an indenegroup, an acenaphthene group, a biphenyl group, a terphenyl group, apyridine group, a pyrimidine group, a pyrazine group, a pyridazinegroup, a triazine group, a quinoline group, an isoquinoline group, aquinoxaline group, a quinazoline group, a phenanthroline group, apyrazole group, an imidazole group, a triazole group, an oxazole group,an isoxazole group, a thiazole group, an isothiazole group, anoxadiazole group, a thiadiazol group, a benzopyrazole group, abenzimidazole group, an imidazopyrazinyl group, a benzoxazole group, abenzothiazole group, a benzoxadiazole group, and a benzothiadiazolgroup.
 4. The organometallic compound of claim 1, wherein: rings A₁ toA₄ are each independently selected from a benzene group, a pyridinegroup, a pyrimidine group, a triazine group, a pyrazole group, animidazole group, a triazole group, a benzopyrazole group, abenzimidazole group, and an imidazopyrazinyl group.
 5. Theorganometallic compound of claim 1, wherein: R₁ and R₂ are eachindependently selected from deuterium, —F, —Cl, —Br, —I, a hydroxylgroup, a cyano group, a nitro group, an amidino group, a hydrazinogroup, a hydrazono group, a substituted or unsubstituted C₁-C₆₀ alkylgroup, a substituted or unsubstituted C₆-C₆₀ aryl group, and asubstituted or unsubstituted C₁-C₆₀ heteroaryl group.
 6. Theorganometallic compound of claim 1, wherein: b5 is
 0. 7. Theorganometallic compound of claim 1, wherein: R₃ and R₁₁ to R₁₆ are eachindependently selected from: hydrogen, deuterium, —F, —Cl, —Br, —I, aphenyl group, a naphthyl group, a biphenyl group, and a terphenyl group;and a phenyl group, a naphthyl group, a biphenyl group, and a terphenylgroup, each substituted with at least one selected from deuterium, —F,—Cl, —Br, —I, a hydroxyl group, a cyano group, a nitro group, an amidinogroup, a hydrazino group, a hydrazono group, a methyl group, an ethylgroup, a propyl group, an isobutyl group, a sec-butyl group, a ter-butylgroup, a pentyl group, an iso-amyl group, a hexyl group, a C₁-C₂₀ alkoxygroup, a phenyl group, a naphthyl group, a fluorenyl group, a pyridylgroup, a pyrimidyl group, a triazinyl group, a quinolinyl group, anisoquinolinyl group, a benzoquinolinyl group, a naphthyridinyl group, aquinoxalinyl group, a quinazolinyl group, a carbazolyl group, adibenzofuranyl group, a benzonaphthofuranyl group, a dibenzothiophenylgroup, a benzocarbazolyl group, and a dibenzocarbazolyl group.
 8. Theorganometallic compound of claim 1, wherein: (i) c1 is 1, and a moietyrepresented by

in Formula 2A or 2B is represented by Formula 4A-1 or 4A-2:

(ii) c2 is 1, and a moiety represented by

in Formula 2A or 2B is represented by Formula 4B-1 or 4B-2:

wherein, in Formulae 4A-1, 4A-2, 4B-1, and 4B-2, Y₁₁, Y₁₂, Y₁₃, Y₂₁,Y₂₂, and Y₂₃ are each independently N or C, *and *′ each indicate abinding site to a neighboring atom, and ^(*1) and ^(*2) each indicate abinding site to M in Formula
 1. 9. The organometallic compound of claim1, wherein: (i) c1 is 1, and a moiety represented by

in Formula 2A or 2B is represented by Formula 4A-1-1:

(ii) c2 is 1, and a moiety represented by

in Formula 2A or 2B is represented by Formula 4B-1-1:

wherein, in Formulae 4A-1-1 and 4B-1-1, Y₁₁, Y₁₂, Y₁₃, Y₂₁, Y₂₂, and Y₂₃are each independently N or C, * and *′ each indicate a binding site toa neighboring atom, and ^(*1) and ^(*2) each indicate a binding site toM in Formula
 1. 10. The organometallic compound of claim 9, wherein: inFormulae 4A-1-1 and 4B-1-1, Y₁₂ and Y₂₂ are each C.
 11. Theorganometallic compound of claim 1, wherein: when at least one of T₁ toT₃ is *—N[(L₅)_(a5)-(R₁₅)]—*′, R₁₅ is a substituted or unsubstitutedC₁-C₆₀ aryl group, or is linked to a neighboring substituent selectedfrom R₁₁ to R₁₄ to form a substituted or unsubstituted C₁-C₆₀heterocyclic group.
 12. The organometallic compound of claim 11,wherein: R₁₅ is a substituted or unsubstituted phenyl group, or islinked to one of L₁ to L₄ to form a substituted or unsubstitutedcarbazole ring or a substituted or unsubstituted azacarbazole ring. 13.The organometallic compound of claim 1, wherein: L₂ is selected fromligands represented by Formulae 3A to 3F:

wherein, in Formulae 3A to 3F, X₁₁ is N or C(R₃₁), and X₁₂ is N orC(R₃₂), L₁₁ to L₂₁ are each independently selected from a substituted orunsubstituted C₃-C₁₀ cycloalkylene group, a substituted or unsubstitutedC₁-C₁₀ heterocycloalkylene group, a substituted or unsubstituted C₃-C₁₀cycloalkenylene group, a substituted or unsubstituted C₁-C₁₀heterocycloalkenylene group, a substituted or unsubstituted C₆-C₆₀arylene group, a substituted or unsubstituted C₁-C₆₀ heteroarylenegroup, a substituted or unsubstituted divalent non-aromatic condensedpolycyclic group, and a substituted or unsubstituted divalentnon-aromatic condensed heteropolycyclic group, a11 to a21 are eachindependently an integer from 0 to 3, Ar₁₁ and Ar₁₂ are eachindependently selected from a substituted or unsubstituted C₃-C₁₀cycloalkyl group, a substituted or unsubstituted C₁-C₁₀ heterocycloalkylgroup, a substituted or unsubstituted C₃-C₁₀ cycloalkenyl group, asubstituted or unsubstituted C₁-C₁₀ heterocycloalkenyl group, asubstituted or unsubstituted C₆-C₆₀ aryl group, a substituted orunsubstituted C₁-C₆₀ heteroaryl group, a substituted or unsubstitutedmonovalent non-aromatic condensed polycyclic group, and a substituted orunsubstituted monovalent non-aromatic condensed heteropolycyclic group,R₃₁ to R₃₂ are each independently selected from hydrogen, deuterium, —F,—Cl, —Br, —I, a hydroxyl group, a cyano group, a nitro group, an amidinogroup, a hydrazino group, a hydrazono group, a substituted orunsubstituted C₁-C₆₀ alkyl group, a substituted or unsubstituted C₂-C₆₀alkenyl group, a substituted or unsubstituted C₂-C₆₀ alkynyl group, asubstituted or unsubstituted C₁-C₆₀ alkoxy group, a substituted orunsubstituted C₃-C₁₀ cycloalkyl group, a substituted or unsubstitutedC₁-C₁₀ heterocycloalkyl group, a substituted or unsubstituted C₃-C₁₀cycloalkenyl group, a substituted or unsubstituted C₁-C₁₀heterocycloalkenyl group, a substituted or unsubstituted C₆-C₆₀ arylgroup, a substituted or unsubstituted C₆-C₆₀ aryloxy group, asubstituted or unsubstituted C₆-C₆₀ arylthio group, a substituted orunsubstituted C₁-C₆₀ heteroaryl group, a substituted or unsubstitutedmonovalent non-aromatic condensed polycyclic group, a substituted orunsubstituted monovalent non-aromatic condensed heteropolycyclic group,—Si(Q₁₁)(Q₁₂)(Q₁₃), —N(Q₁₁)(Q₁₂), —B(Q₁₁)(Q₁₂), —C(═O)(Q₁₁),—S(═O)₂(Q₁₁), and —P(═O)(Q₁₁)(Q₁₂), R₃₁ and R₃₂ are optionally linked toform a saturated or unsaturated ring, and R₃₃ and R₃₄ are optionallylinked to form a saturated or unsaturated ring, X₂₁ is selected from —F,—Cl, —Br, and —I, *″ indicates a binding site to M in Formula 1, atleast one substituent of the substituted C₃-C₁₀ cycloalkylene group, thesubstituted C₁-C₁₀ heterocycloalkylene group, the substituted C₃-C₁₀cycloalkenylene group, the substituted C₁-C₁₀ heterocycloalkenylenegroup, the substituted C₆-C₆₀ arylene group, the substituted C₁-C₆₀heteroarylene group, the substituted divalent non-aromatic condensedpolycyclic group, the substituted divalent non-aromatic condensedheteropolycyclic group, the substituted C₁-C₆₀ alkyl group, thesubstituted C₂-C₆₀ alkenyl group, the substituted C₂-C₆₀ alkynyl group,the substituted C₁-C₆₀ alkoxy group, the substituted C₃-C₁₀ cycloalkylgroup, the substituted C₁-C₁₀ heterocycloalkyl group, the substitutedC₃-C₁₀ cycloalkenyl group, the substituted C₁-C₁₀ heterocycloalkenylgroup, the substituted C₆-C₆₀ aryl group, the substituted C₆-C₆₀ aryloxygroup, the substituted C₆-C₆₀ arylthio group, the substituted C₁-C₆₀heteroaryl group, the substituted monovalent non-aromatic condensedpolycyclic group, and the substituted monovalent non-aromatic condensedheteropolycyclic group is selected from: deuterium, —F, —Cl, —Br, —I, ahydroxyl group, a cyano group, a nitro group, an amidino group, ahydrazino group, a hydrazono group, a C₁-C₆₀ alkyl group, a C₂-C₆₀alkenyl group, a C₂-C₆₀ alkynyl group, and a C₁-C₆₀ alkoxy group; aC₁-C₆₀ alkyl group, a C₂-C₆₀ alkenyl group, a C₂-C₆₀ alkynyl group, anda C₁-C₆₀ alkoxy group, each substituted with at least one selected fromdeuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group, a nitrogroup, an amidino group, a hydrazino group, a hydrazono group, a C₃-C₁₀cycloalkyl group, a C₁-C₁₀ heterocycloalkyl group, a C₃-C₁₀ cycloalkenylgroup, a C₁-C₁₀ heterocycloalkenyl group, a C₆-C₆₀ aryl group, a C₆-C₆₀aryloxy group, a C₆-C₆₀ arylthio group, a C₁-C₆₀ heteroaryl group, amonovalent non-aromatic condensed polycyclic group, a monovalentnon-aromatic condensed heteropolycyclic group, —Si(Q₁₁)(Q₁₂)(Q₁₃),—N(Q₁₁)(Q₁₂), —B(Q₁₁)(Q₁₂), —C(═O)(Q₁₁), —S(═O)₂(Q₁₁), and—P(═O)(Q₁₁)(Q₁₂); a C₃-C₁₀ cycloalkyl group, a C₁-C₁₀ heterocycloalkylgroup, a C₃-C₁₀ cycloalkenyl group, a C₁-C₁₀ heterocycloalkenyl group, aC₆-C₆₀ aryl group, a C₆-C₆₀ aryloxy group, a C₆-C₆₀ arylthio group, aC₁-C₆₀ heteroaryl group, a monovalent non-aromatic condensed polycyclicgroup, and a monovalent non-aromatic condensed heteropolycyclic group; aC₃-C₁₀ cycloalkyl group, a C₁-C₁₀ heterocycloalkyl group, a C₃-C₁₀cycloalkenyl group, a C₁-C₁₀ heterocycloalkenyl group, a C₆-C₆₀ arylgroup, a C₆-C₆₀ aryloxy group, a C₆-C₆₀ arylthio group, a C₁-C₆₀heteroaryl group, a monovalent non-aromatic condensed polycyclic group,and a monovalent non-aromatic condensed heteropolycyclic group, eachsubstituted with at least one selected from deuterium, —F, —Cl, —Br, —I,a hydroxyl group, a cyano group, a nitro group, an amidino group, ahydrazino group, a hydrazono group, a C₁-C₆₀ alkyl group, a C₂-C₆₀alkenyl group, a C₂-C₆₀ alkynyl group, a C₁-C₆₀ alkoxy group, a C₃-C₁₀cycloalkyl group, a C₁-C₁₀ heterocycloalkyl group, a C₃-C₁₀ cycloalkenylgroup, a C₁-C₁₀ heterocycloalkenyl group, a C₆-C₆₀ aryl group, a C₆-C₆₀aryloxy group, a C₆-C₆₀ arylthio group, a C₁-C₆₀ heteroaryl group, amonovalent non-aromatic condensed polycyclic group, a monovalentnon-aromatic condensed heteropolycyclic group, —Si(Q₂₁)(Q₂₂)(Q₂₃),—N(Q₂₁)(Q₂₂), —B(Q₂₁)(Q₂₂), —C(═O)(Q₂₁), —S(═O)₂(Q₂₁), and—P(═O)(Q₂₁)(Q₂₂); and Si(Q₃₁)(Q₃₂)(Q₃₃), —N(Q₃₁)(Q₃₂), —B(Q₃₁)(Q₃₂),—C(═O)(Q₃₁), —S(═O)₂(Q₃₁), and —P(═O)(Q₃₁)(Q₃₂), and Q₁ to Q₃, Q₁₁ toQ₁₃, Q₂₁ to Q₂₃, and Q₃₁ to Q₃₃ are each independently selected fromhydrogen, deuterium, —F, —Cl, —Br, —I, a hydroxyl group, a cyano group,a nitro group, an amidino group, a hydrazino group, a hydrazono group, aC₁-C₆₀ alkyl group, a C₂-C₆₀ alkenyl group, a C₂-C₆₀ alkynyl group, aC₁-C₆₀ alkoxy group, a C₃-C₁₀ cycloalkyl group, a C₁-C₁₀heterocycloalkyl group, a C₃-C₁₀ cycloalkenyl group, a C₁-C₁₀heterocycloalkenyl group, a C₆-C₆₀ aryl group, a C₁-C₆₀ heteroarylgroup, a monovalent non-aromatic condensed polycyclic group, amonovalent non-aromatic condensed heteropolycyclic group, a biphenylgroup, and a terphenyl group.
 14. The organometallic compound of claim1, wherein: the organometallic compound is selected from Compounds 1 to42:


15. An organic light-emitting device comprising: a first electrode asecond electrode facing the first electrode; and an organic layerbetween the first electrode and the second electrode and comprising anemission layer, wherein the organic layer comprises at least one of theorganometallic compound of claim
 1. 16. The organic light-emittingdevice of claim 15, wherein: the first electrode is an anode, the secondelectrode is a cathode, the organic layer further comprises a holetransport region between the first electrode and the emission layer andan electron transport region between the emission layer and the secondelectrode, the hole transport region comprises a hole injection layer, ahole transport layer, an emission auxiliary layer, an electron blockinglayer, or any combination thereof, and the electron transport regioncomprises a hole blocking layer, an electron transport layer, anelectron injection layer, or any combination thereof.
 17. The organiclight-emitting device of claim 16, wherein: the organometallic compoundis comprised in the emission layer, the emission layer further comprisesa host, and an amount of the host in the emission layer is larger thanan amount of the organometallic compound in the emission layer.
 18. Theorganic light-emitting device of claim 16, wherein: the electronblocking layer or the hole blocking layer comprises the organometalliccompound.
 19. The organic light-emitting device of claim 17, wherein:the host comprises at least one of a silicon-containing compound and aphosphine oxide-containing compound.
 20. The organic light-emittingdevice of claim 16, further comprising a capping layer on the firstelectrode or the second electrode, wherein the capping layer comprisesthe organometallic compound.